


Then He Came Along

by itsnotofimport



Category: Supernatural
Genre: Age Difference, Alternate Universe - Modern Setting, Angst, Benny is in love with Dean, Bottom Castiel/Top Dean Winchester, Broken Hearts, Canonical Character Death, Castiel & Meg Masters Friendship, Castiel Loves Dean Winchester, Cheating, Dean Winchester Being an Asshole, Dean in Denial, Dom/sub Undertones, Domestic Fluff, Domestic Pinning, Everyone Is Gay, Exhibitionism, F/F, First Times, Fluff, Gay Bashing, Gay Castiel, Gay Dean Winchester, Happy Ending, Hurt Castiel, Lawyer Dean Winchester, Lawyer Sam Winchester, M/M, Open Relationships, POV Alternating, QAF AU, Rimming, Sassy Castiel, Smut, Student Castiel, Threesome - M/M/M, Twink Castiel, bad fathers, pianist castiel
Language: English
Status: In-Progress
Published: 2016-08-24
Updated: 2017-01-11
Packaged: 2018-08-10 18:51:35
Rating: Explicit
Warnings: Underage
Chapters: 10
Words: 28,234
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7857061
Author URL: https://archiveofourown.org/users/itsnotofimport/pseuds/itsnotofimport
Summary: <blockquote class="userstuff">
              <p>Dean Winchester always said, "Monogamy is for women," and he was once completely happy living out his years with a different man in his bed every night. Until the night he met 17 year old Castiel Novak, the kid wormed his way into Dean's life in ways Dean never thought possible.</p>
            </blockquote>





	1. Chapter 1

As long as Castiel Novak could remember he had been locked away in his ivory tower. Growing up in New Jersey to one of the richest families in the state had it's challenges. He was sheltered and often lonely, Castiel had four much older siblings but he was, what you would call, an accident. At least his parents Amelia and James called him that, the doctors called him a miracle. Long story short when Castiel was born the youngest Novak kid, Anna, was already in high school. Amelia and James hadn't planned on having another kid, they didn't think Amelia could have other kids, but then came along Castiel. Their little accident. 

Amelia doted on Castiel in a way she never did with her other children. Michael, Zack, Gabriel and Anna were all very close in age and never got the kind of attention Castiel was given growing up. At a young age Amelia decided that Castiel should become some sort of prodigy. At age five she placed him into piano lessons because her psychic said Castiel Novak would become a famous pianist one day. Sure it sounded crazy, and Castiel guessed it was but that had become his life.

Everyday piano lessons, every day studying for good grades to get into a good college. It left very little room for error or as most people called it; _fun_. When Castiel started high school Amelia thought it was best to move to New York City so Castiel could attend the Fiorello H. LaGuardia High School Of Music  & Art and Performing Arts. That's where he met his now best friend Meg Masters. Meg was a sassy violinist, and everything Castiel needed in his life.

“It’s a school night Castiel!” Meg gawked at her best friend. "Usually I'd condone this behavior but this is so left field coming from you."

“Don’t care. I’m seventeen years old and still a virgin, I want to get laid. I _need_ to get laid Meg,” Castiel bounced happily on his feet, “I’m going out.”

“And how are you going to get into a gay bar?” Meg raised an eyebrow and folding her arms across her chest.

Castiel hadn’t gotten that far into his plan. So far his plan consisted of telling his mother he was staying the night at his friend Garth’s house, going out to a bar, and finding an older, attractive, experienced man to pop his ass cherry. Nothing could go wrong. Realistically he wasn't that close to Garth at school, it's just the name Castiel used as an excuse to go to Meg's house. His mother would never allow Castiel to spend the night at a girl's house. His mother also didn't know he was gay, Meg's parents did know. The Masters were cool unlike Castiel's old conservative parents.

“I’ll figure something out when I get there. Maybe wait outside for someone if I can't get in.” Castiel shrugged.

“I believe you’ll have no problem getting some old dude to fuck you, I’m just worried about it.” Meg watched as Castiel as he changed his clothes, the teen slipping into something more appropriate for scouting. Although on second thought his school uniform would also probably do the trick if the porn he watched was anything to go on.

“I know that, I’m a twink Meg. Old dudes love twinks.” Castiel winked at her.

“You’re underage, not a twink.” Meg corrected, “And how old are we talking here unicorn?” She grimaced, trying not to picture her best friend being butt fucked by an old hairy fat guy.

“Maybe like thirty? Someone handsome,” Castiel had daydreamed many times what his first time would be like. He'd prefer to be in love but being a closeted high school student didn't leave room for dating and falling in love. The man needed to be handsome, Castiel pictured someone nice and good-looking enough to pass as a Disney prince. Was it unrealistic? Sure, but Castiel could dream. He was, after all, a romantic.

“Just don’t get your hopes up, picking up a guy for a one night stand isn’t exactly all it’s cracked up to be.” Meg threw caution to the wind, of course it had fell on deaf ears.

“And how would you know? You’ve only given like two blow jobs in your life and one of them was me and I didn’t even get hard.” Castiel glared.

“Well that wasn’t my fault, that was all you sweet cheeks.”

There was no denying that. Castiel really loved Meg but she didn’t have the right gear that got him going.

* * *

 

Dean Winchester swaggered across the bar still buttoning up his grey dress pants. It was one of those nights where Dean just could not become satisfied. He'd already gotten two blow jobs in the back room from two different men. Dean was still hungry for more, he just wasn't sure what yet. 

Dean liked to think he lived a very simple life. Him and his brother Sam owned a very successful law firm in Manhattan. Sure he often got called a scumbag for the types of rich clients he'd represent, but going home to his penthouse every night seemed to turn the negativity into white noise. If you were to ask Dean why he hasn't settled down, how come he hasn't found the love of his life at twenty-nine, being so rich and handsome; well, he'd say, "Because that shits for chicks". 

Dean didn't believe in love, he believed in fucking. 

“Dean Winchester I don’t know how you do it,” Benny pressed a sloppy kiss to his best friend’s cheek.

“I know what I like and I go after it, these cock sluts love that.” Dean winked at a man down a couple seats at the bar. The guy immediately smirked, giving Dean the all knowing ‘Hey wanna fuck?’ look. Dean chuckled and downed his shot, never looking away from the guy.

“Seriously Dean? You literally just got your dick sucked in the bathroom two minutes ago!” Cole shouted in outrage from the other side of Benny.

“It’s been at least five Trenton. I’m a shark, I gotta keep my dick wet.” Dean wiggled his eyebrows at his friends.

Cole shook his head, “I have to talk with a guy for hours, buy him all the damn drinks he wants so I can convince them to head home with me, Dean just gotta look at a guy.” Dean smirked, Cole's Queen's accent really came out when he was drunk. It entertained Dean endlessly. He had a thing for accents.

“Fellas!” A drunken Aaron came up to Dean wrapping his arms around his neck, kissing Dean soundly on the mouth.

“Oh look everyones favorite gay jew.” Dean tried to get Aaron to stand up straight. Aaron chuckled, “I’m going to get laid tonight boys, just wait and see.”

“You say that every night,” Benny rolled his eyes.

“And you always end up alone.” Cole followed.

“Aw leave him alone boys, he tries his hardest,” Dean pinched Aaron's cheek.

“Yeah we can’t all be Dean Winchester.” Aaron rolled his eyes.

"No you cannot." Dean ordered yet another drink. The night was still young.

* * *

“I can’t believe they just let us in!” Castiel was still in shock. The bouncer at the front door hadn't even bothered to check their ID's.

“I think it’s because you look like… _that._ ” Meg eyed his outfit.

Castiel went for a black mesh top and red pants that were way too tight on him. His hair was spiked and wild in a way that Meg could only describe as ridiculous.

“I needed to look gay.” Castiel shrugged.

“And that you do my friend,” Meg searched through the guys in the crowded bar. “See anyone you like?”

Castiel looked around, “Hm not yet,” He turned towards Meg, “Remember you’re only staying until I find someone.”

“Yeah, yeah and get his name and address,” His over protective friend smirked.

* * *

“Tonight is boring, I feel like I’ve fucked everyone in here,” Dean scrunched up his nose in distaste. “I need a new crowd.”

“You probably have fucked everyone in here, more than once.” Benny commented.

Dean snapped his head at his best friend, “Bullshit, you know my rule. I never fuck anymore more then once.” Dean shivered at the thought. Dean could never imagine having a relationship, fucking one person for the rest of your life? That shit was for women. Women who trapped men or women who liked other women. Dean was a man who loved loving other men, well their bodies. There was no need to go on dates and fall in love. The idea almost made him sick.

But then, the crowd parted. Dean sat up straighter in his bar stool when he saw _him._ The moment felt like Dean was Moses, the crowd of glittery gays were the red sea, and the beautiful dark haired twink on the other side of the room, he was freedom. Maybe not Dean's best analogy but he didn't care, his night just became interesting.

“Sorry Benny, I think you’re going to have to call a cab. I just found freedom.” Benny raised an eyebrow at Dean.

“C’mon Dean don’t ditch me again.” Dean was Benny’s ride. One would think Benny should learn his lesson and stop trusting Dean to not leave him at the bar for a piece of ass. But this was Dean, and Dean was an asshole and Benny was Benny, he'd follow Dean to the end of the Earth. Everyone knew that, including Dean.

“Sorry man, I just caught eye of a beautiful specimen.” He looked at Benny seriously, “I must fuck it.”

Dean staggered off leaving his pissed off friend at the bar.

“Hello.” Dean smiled at the beautiful blue eyed creature before him. He was skinny but had some muscle to him with thick thighs, Dean could see his small nipples through the mesh of his shirt. Fuck, he was perfect.

“Hi,” blues eyes answered shyly. Dean quirked an eyebrow at his voice, it was deeper then he thought it would be. It was obvious however he was still developing and his voice would only get deeper as he got older. Dean placed him at about age nineteen. He was usually never wrong about these things.

“My name's Dean.” Dean trailed his eyes down the twink’s body again, making it clear what he wanted.

“I’m Cas.” Dean knew he wouldn’t remember that. Only Dean's name mattered, and this twink would be screaming it by the end of the night. Dean would make sure of it.

“How old are you Cas?” Dean’s eye’s flicked down to his perfectly shaped lips, he smirked when Cas licked his lips at the attention.

“I’m nineteen. I go to NYU.” Dean mentally high-fived himself for guessing Cas’ age right. 

“I didn’t ask where you went to school. Don’t oversell yourself kid.” Dean ran an uninvited hand down Cas’ chest.

“Don’t call me kid if you want to fuck me.” Cas shot back pushing Dean’s away from traveling any lower.

Dean laughed, “I like you, wanna come home with me?” Dean knew the answer. People didn’t tell him no.

“No.” Said a female voice from next to the sexy blue eyed twink, Dean hadn't noticed her before. “You’re too arrogant. He's no good Cas,” She said.

Fuck, he had a watch dog. Dean hated those, usually nosey dikes or fag hags who hung too close to their gay friends. Women never let men be men.

“Meg,” Cas snapped at her, “It’s fine. I’m leaving with him.” 

A mental fist pump from Dean was necessary. He wanted to stick his tongue out at the annoying friend but then remember he was thirty and better then that, but not really so he did it anyway. The friend didn't seemed too amused. However the twink laughed. Dean eyed him once more, he really would do lovely for the night.

“Yeah _Meg_ , he wants to leave with me.” A cocky smile directed towards her, one to end her slaughter.

“What’s your name? Full name.” She folded her arms over her chest. God Dean hated women.

“Dean Winchester. I’m a lawyer and not a murderer. Now if you don’t mind, I would like to fuck your friend here.”

Dean didn’t let bitch face answer, he tugged on Twink's hand and pulled him outside of the bar.

“I don’t live too far from here,” Dean had let go of blue eye’d twinks hand. Dean didn’t look to see if the man was following him to his car, he just knew he was.

“You are kind of arrogant,” Twink spoke as they walked through the parking lot, “I guess you’re probably used to getting what you want. With your looks and all.”

They reached the impala and Dean turned quickly to face Twink. “I am used to getting what I want, and I want you.” Dean grabbed the collar of Twink’s shirt pulling him into a dirty kiss, his forceful tongue finding it’s way into his mouth, calming him for the night. Twink responded rather eagerly, Dean loved when they were enthusiastic.

Dean pushed Twink away, “Looks like I’m getting what I want again tonight.” He smirked. “Get in the car.”

* * *

“Wow,” Castiel was dumbfounded by Dean’s apartment. The penthouse wasn’t necessarily huge, but it was nice. The living room, dinning room, and kitchen were all opened spaced making one grand room. Castiel always lived in very large houses, some would say mansions but he had never been inside a penthouse like Dean's. 

"You have a piano!" Castiel's eye's lit up as he made his way over to the large white grand piano in the corner of the room.

"I don't play it, it's just for show." Dean sounded unamused, "You play?" To Castiel it sounded like Dean was trying too hard to care, so he didn't answer.

Next to the piano were modern looking white couches, Cas sat on the largest one. placed in the middle of two smaller ones. In front of the couch the wall was lined with large windows and a view of the hudson river.

“Great view.” He watched the New York City lights for awhile.

Dean cleared his throat. “My bedroom is upstairs, if you want to get moving.” Dean didn’t sound impatient anymore, he sounded slightly more amused.

“Yeah sure,” Castiel followed Dean up a spiral stair case into a half walled room that opened up into the living space below. Dean had a nice king size bed, with decor that matched the rest of the penthouse. Everything was black, white and gold. All modern styles. Cas thought the place should be in an interior design magazine.

Dean disappeared behind a door that could only be the bathroom. Cas leaned over the half wall and looked down at the couch he was just sitting at. The view from the large windows was even nicer from the upstairs.

Castiel jumped when he felt a hand on his hip. He turned towards Dean, a smirk playing on the older mans face.

“Sorry, didn’t mean to scare you.” Dean pushed his hand under Castiel’s mesh shirt, his fingers dancing along his ribs. Cas couldn’t take his eye’s off of Dean, they were an amazing shade of green. Castiel felt almost hypnotized by them. Good thing Dean didn’t seemed bothered with eye contact, it seemed more like he got off on it. Watching Castiel with an intensity that made him shutter.

Dean removed Castiel’s shirt and started kissing down his chest, wasting no time to fall down onto his knees, hands flying to undo his red jeans, Dean sucked on his hipbones as he worked his pants down. Castiel’s jeans were so tight they brought his boxers down with them.

And It was actually happening, Castiel was standing stark ass naked with a _very_ handsome man kneeling in front of him. Castiel’s breathing picked up when Dean began placing wet opened mouthed kisses from his hip towards his half erected cock.

Dean smiled up at Cas before wrapping his large hand around the base. Castiel fumbled at the touch, biting his lip and watching Dean in awe.

Dean flicked his tongue over the tip of Castiel’s cock before sucking on it gingerly. Castiel gasped at the sensation, the feeling was completely different from Meg’s failed blowjob from last year. 

Dean took Castiel’s cock in his mouth like a pro. Castiel thought Dean could be a porn star with the way he was moving up and down his shaft. Deep throating like he’s only ever seen his favorite porn stars do.

Castiel groaned thrusting his hips forward, trying to move with the speed of Dean's mouth. Castiel felt a hum around his cock, he wasn't sure if it was Dean laughing or his approval of Castiel's moment.

Dean popped off Castiel’s cock with a line of saliva hanging from his chin, it didn’t seem to bother him as he just wiped if off with the back of his hand. Dean rose from his kneeled position and placed his hand behind Castiel’s neck pulling him into a deep kiss, his other hand wrapped around Castiel’s lower back. This kiss had been different then their first. This kiss was all controlled moments, a seduction from Dean that drove Castiel nuts.

Cas moaned into the kiss, he had never been kissed so throughly, it felt like Dean was fucking his mouth with his tongue and Castiel struggled to keep up.

The teen tried his hardest not to trip over the jeans around his ankles as Dean walked them backwards towards the bed. Dean was skilled in maneuvering them without breaking their kiss. Castiel only became more and more impressed by the experienced man. 

Cas felt the bed hit the back of his knees and Dean gave him a little shove telling him silently to sit down.

“Take your shoes and the rest of your pants off,” Dean ordered, his voice rougher then before, his hands moving fast to remove his clothing until he was naked.

Castiel struggled to get his shoes off at first, Dean just watched him with his head titled, his right hand lazily stroking his cock to hardness.

* * *

As Dean watched Twink nervously remove his shoes and pants, he could think of nothing but those lips wrapped around his cock.

And as Twink said earlier, Dean got what he wanted. Dean stepped forward next to the bed between Twink’s legs. Twink’s face was eye level with Dean’s hard on. Dean knew most people were intimitanted by Dean’s size at first, some just needed a little encouraging. 

Dean placed his hand on the back of Twink’s head the other gripping the base of his cock. Dean held Twink’s head still as he ran the tip of his dick over those beautiful lips. Dean chuckled when Twink’s tongue darted out, desperate for a taste.

Dean couldn’t deny those blue eyes anything so he pushed the head of his cock into Twink’s hot mouth. Twink sucked on the tip and it was heaven. Dean wanted nothing more then to face fuck the innocent look off of Twink’s face, but Dean had a good read on people he knew Twink couldn’t handle that.

Dean let Twink set his own pace, he was unable to get all of Dean’s cock in without gagging. But some of the best cocksuckers he knew had problems with that.

It wasn’t Dean’s best blowjob but what Twink lacked in talent he made up for in enthusiasm. Twink had managed to get Dean hard and wet and Dean would say that was a job well done.

“Stop now,” Dean dropped his hand away from the back of Twink’s head. Twink greedily sucked Dean down as far as he could one more time before moving away.

“Ready?”

Twink nodded enthusiastically. Perfect.

**Notes for the Chapter:**

> This fic is based off the of TV show Queer As Folk. You'll see similar characters and storylines.


	2. Chapter 2

" _Dean!_ " Cas moaned, hands gripping the bed sheets as Dean's thick fingers continually brushed against his prostate. If Castiel had not been in absolute bliss, he might've rolled his eyes at the smug smirk on Dean’s face.

“You’re so responsive,” Dean growled seductively, his three fingers rubbed against Castiel’s sensitive gland again forcing another loud moan out of the teen, this time his back involuntarily arching searching for that deeper stretch.

Dean leaned down taking Castiel’s right nipple into his mouth, swirling his tongue and nipping at it, hardening the bud. His eye's never leaving Castiel's face, it was obvious Dean enjoyed watching the pressure he gave to his lovers. 

“ _Ah_.” Castiel let out a shaky breath. Until tonight, he had no idea his nipples were so sensitive, the teen had almost reached the point of sensory overload. With three fingers pumping roughly in and out of him and the feeling of Dean’s hot mouth trailing along his chest and teasing his nipples, giving them attention they never had before. It was all too much for someone with very little sexual experience and Dean was _skilled_ , he knew exactly what he was doing and how to turn Castiel on. The blue eyed boy had no choice but to just lay there in the mercy of this sex god.

A loud vibrating noise came from the nightstand just right of Castiel's head. 

“Ugh.” Dean huffed out clearly irritated as he moved his mouth away from the insult on Castiel’s nipples. Around Dean a light illuminated the darkened bedroom, almost giving the older man a halo. Still three fingers deep and lazily fingering Castiel, Dean answered his phone.

“Fucking what Benny? I’m busy!” Dean snapped into the phone titling his head balancing the phone on his shoulder freeing up his left hand.

Dean frowned his eyebrows as he listened to what this Benny guy was saying on the other line. He glanced down at Castiel briefly before thoughtlessly wrapping his left hand around the teen's cock moving his it up and down the shaft in time with the pumping of his fingers.

Castiel bit back a moan, oddly not wanting to interrupt Dean’s phone call.

“Well if you must know Benny I’m three fingers deep in that cute little twink I picked up,” Dean winked at Castiel, and it was probably the weirdest moment of Castiel’s young life.

Castiel’s mouth hung open in a silent scream as Dean put pressure on his prostate, he couldn’t believe the man currently sat between his legs actually existed. Dean gripped Castiel's cock tighter forcing a loud groan from his young mouth.

Dean smiled, “Hear that?” he said into the phone, “All me bro.” 

Castiel was so close and was way too wrecked to warn Dean verbally so he started smacking him lightly on his forearm. Castiel went on being ignored as the hand that arm belonged to collected the pre-cum from Castiel’s tip, jacking him off harder. 

“Why the fuck didn’t you open with that?” Dean said angrily into the phone. Completely unknowingly how he was unraveling Cas. "And why the fuck anybody call me sooner?"

“Ah _Dean_!” Castiel came hard all over his chest and Dean’s hand, his body twitching from the strongest orgasm he's ever had.

“Oh fuck,” Dean glared down at Castiel’s cock as if it had personally offended him.

“No not you Benny.... I’ll be there as soon as I can.” Without his hands Dean let the phone drop onto his bed. Next to Castile's hip.

“I gotta go,” Dean said as he removed his fingers, reaching towards his nightstand grabbing a few tissues to clean them both up with.

“Wh-what do you mean?” Castiel's voice was embarrassingly shaky.

“I mean I gotta go. Good thing you came I would’ve felt bad otherwise. Get dressed and get out.” Dean got up from the bed stalking towards his bathroom leaving Castiel naked and sweaty on the bed.

Castiel was dressed by the time Dean came out of the bathroom. There must’ve been a closet attached to the bathroom because Dean had gotten dressed in different clothes from earlier. He looked younger, he had on well wore jeans and a tight fitting band t-shirt. Castiel definitely liked this look better then the dress shirt and slacks still on Dean's bedroom floor.

“Why are you still here? I told you to leave.” Dean was moving around his room fanatically looking for something.

“I-I told my mo-roommate that I would be out all night and he has someone over too so I can’t go back to my dorm tonight," the teen lied almost effortlessly. "Can I come with you? I have no where to go.” Castiel twisted his fingers together nervously.

“Ah ha!” It seemed Dean found what he was looking for as he held up his car keys. He turned towards Castiel with a grumpy look on his face and sighed, “You can come, but only if I can fuck you later.”

Castiel nodded, “Yes, yes that’s good. Great.” Castiel cursed himself silently for sounding like an idiot in front of the hottest man in the world.

“All right then, pull your pants down and bend over,” Castiel stood in shock at the request, “Hurry now, we gotta go.” Dean snapped his fingers.

Dean moved back into the bathroom, Castiel could hear him digging for something. The teen embarrassingly followed the older mans instructions.

Castiel let his jeans his and boxers pool at his feet, he bent over placing his palms flat on the bed, sticking his ass out. 

Dean chuckled when he walked back into the bedroom, “Submissive little thing aren't you?” Castiel watched Dean as he grabbed the bottle of lube off the nightstand.

“This is a butt plug, I imagine you know what that is,” Dean showed Castiel the purple toy with a gem on the end, Castiel stared at it and slowly nodded his head. “You’re going to wear it so when we get back here I can go straight to fucking you. Don’t worry, it’s clean.”

Dean stood staring at Castiel, finally the teen realized Dean was waiting for consent.

“Okay.” Castiel said with fake confidence. The night had turned out way more interesting then Castiel had originally hoped for and he couldn’t wait to tell Meg about it. About  _him._

Dean moved behind Castiel, instantly the teen felt two lubed fingers rub against his already loosened hole. Dean quickly pushed the fingers inside twisting them and making sure Castiel was ready for the toy.

Castiel groaned as Dean removed his fingers and the feeling the butt plug teased his entrance.

The teen moaned and hung his head as the toy was slowly pushed in. Dean wiggled in place before stepping back. Cas could feel Dean’s eyes on him. His hole body burned from the attention of the godly man.

“Damn you’ve got a great ass,” Dean smacked Castiel’s right ass cheek making him jump.

“Pull your pants back up, we gotta go,” Dean laughed at Castiel’s careful movements, he almost sounded evil.

“Can I borrow a shirt, this one is-“ Castiel looked down at his mesh shirt while buttoning up his pants, wincing slightly at the way the butt plug felt inside of him.

“Yeah I suppose you can’t wear that where we’re going,” Dean disappeared into bathroom again.

Where were they going?

Dean returned and threw a black Led Zeppelin shirt at Castiel’s face, Cas removed his mesh shirt and pulled on Deans. It smelled fantastic, all manly and musky but clean. Castiel knew it was a smell he wouldn't be forgetting soon. Dean chuckled, clearly amused by how the shirt hung on Castiel’s smaller frame.

“So where are we going?” Castiel followed Dean closely behind and into his penthouse elevator.

“Neverland.” Dean mumbled in response.

**Notes for the Chapter:**

> Episodes of Friend's are inspiring the chapter titles. I'll regret chapter naming soon enough.


	3. Chapter 3

Dean was two minutes away from chloroforming Twink. As far as patience goes, Dean had very little, and Twink was pushing it.

Benny lived only a ten minute drive from Dean's apartment , the car ride to pick him up should have been effortless if it weren’t for Twink running his damn pretty mouth non stop. Dean stopped listening at soon as he started talking - something about bees, something about the piano, something, something, something. Dean convinced himself that Twink wasn’t human, he wasn’t sure the last time he heard the kid take a breath.

“So anyway, like I was saying, Garth at school - he’s the one I told you about earlier, the funny one - HE stood up in the middle of class or I mean in the middle of a lecture and just-" Dean’s hand flew over Twink’s mouth.

“You look and sound better with a cock in your mouth,” Dean pulled his hand away when Twink thought it was cute to lick his palm, it was pretty cute Dean had to admit to himself. “Do you ever stop talking?”

Twink shrugged, “Meg says I talk to much because I’m not socialized enough. I hide in my room so much that when I finally have someone to talk to I just go on and on.”

Dean gripped the steering wheel tight and gritted his teeth, “Your ass better be worth my pain and suffering.”

“Oh, sorry if I’m being annoying,” Twink turned his head to look out the passenger window. Okay, so Dean felt a little bad for the kid. “You can tell me to shut up, it won’t hurt my feelings.”

“I did tell you to shut up, about five fucking times.” Dean wanted to snap at him, but he ended up sounding playful instead.

Out of the corner of Dean's eye he could see Twink turn his head back towards Dean, smirking at him and _great_ now he was staring.

“I really like your car.” Twink spoke again. 

“Thanks.” Dean caught Twink’s eye briefly. It seemed Twink was finally done speaking, Dean’s bleeding ears got a moments rest.

* * *

 The car slowed and it appeared to Castiel that they had reached where ever they were headed. Dean pulled his car over towards a curb in front of an old building. It definitely wasn't as nice as Dean's, but Cas knew even an old building like this cost a lot in Manhattan.

There was a very built man in a cap sitting on the steps of the buildings stoop. Castiel sort of recognized him from the bar. The large man hurried his way to the passenger door and flung it open, stopping to glare at Castiel.

“What the fuck Dean? You’re bringing your one night stand?” Castiel titled his head at the man’s accent. He definitely wasn’t from New York. Dean himself sounded a little southern but this man was very southern. "Get in the back," the man told Cas, before Castiel's could move Dean spoke again

“You just get in the back Benny.” Dean sounded like he had lost all patience, Castiel knew that was mostly his fault for talking so much. Still a small smile of triumph reached his lips, Dean could have easily made Castiel sit in the back. As it was Castiel was having to sit funny due to the toy in his ass, he was grateful he didn't need to move.

“God damnit.” Benny slammed the passenger door closed and climbed into the back.  
  
As Dean took off again Castiel turned in his seat to look at Benny in the back, “Hello. I’m Castiel.”

“Castiel?” Dean questioned. It had been obvious to Cas that Dean hadn’t remembered his name. Cas felt a little hurt by it, but he knew the kind of man Dean was, and Dean wasn’t going to ever remember Castiel’s name. Cas made it his mission to get him to remember it.

Benny chuckled, “I’m Benny.” Castiel wasn't great at reading people but he could tell Benny didn't like him, at all. “I still can’t believe you’re fuckin’ bringing him. You’re an idiot, Sam’s gonna have your ass.” Benny shook his head at Dean.

“Where are we going?” Castiel asked for what felt like the fifth time that night.

Benny laughed, throwing his head back, “You didn’t tell him? Kid you’re in for a surprise.”

“Shut up Benny.” Dean rolled his eyes and glanced an almost apologetic stare.

“So where are you from Benny?” Castiel had already guessed Louisiana, he watched a lot of Croc Hunters and knew a cajun accent when he heard one.

“Louisiana.” Benny answered but seemed very uninterested in speaking to Castiel.

“Is that where you’re from also Dean?” 

“No. I’m originally from Kansas.” Dean answered with the same tone as Benny. Honestly Castiel was surprised he got an answer at all.

“Cool. I was born and raised in Jersey. My family and I moved here a few years ago. Better schools.” Castiel shared to an uncaring crowd.

“I can tell by your accent you’re from New Jersey.” Castiel smiled, happy that Dean was finally engaging in conversation.

“Really? I don’t think I have one.” The teen responded trying to keep the conversation going.

“You say some things funny. You don’t sound like the douchbags from Jersey Shore but you’re definitely from Jersey.”

Cas chuckled, “My family is also Russian so I guess I do say some things funny.”

There was a pause in the conversation when Dean didn’t respond. “I think you say somethings funny too,” Castiel ignored the annoyed huff from the backseat, “Like the word _things_ , you say ‘ _thangs_ ’. I noticed that earlier, it’s really cute.”

Dean rolled his eyes, “Jesus Christ.” He mumbled, it was barely audible but Cas still heard it.

 

* * *

“The hospital?”

“Why are we at the hospital Dean?” Cas felt sudden panic, what if they were visiting a dying relative of Dean's? Castiel in himself was already very awkward, that scenario would take the awkward cake.

Neither man answered as they walked into the hospital and took the elevator to the third floor. The labor and delivery floor.

“Someone’s having a baby?” Castiel struggled to keep up with Dean and Benny, they were practically racing down the hospital corridors. Castiel could've kept up better if he didn’t have a blunt object in his ass.

“Ah! Room 314,” Benny stopped to open the closed door. Castiel naturally followed Dean into the room, not really knowing what else to do.

“It’s about damn time you showed up!” A blonde woman glared at Dean. She was in a hospital gown and looked like she just… well, had a baby.

“I’m sorry Jess, I was caught up.” Dean walked over placing a kiss on her forehead.

“Only Dean Winchester would arrive late to the birth of his own niece.” A very tall man with long hair shook his head.

“Look at you princess,” Dean cooed at the tiny baby in the blondes arms. Castiel felt a burst of warm in his chest. Dean had been so stoic but seductive all night, this man looked completely different. His face lit up and softer as he wiggled a finger at the tiny baby.

“I had to pick up Benny, get off my back.” Dean finally answered the tall man.

“Plus it’s not like I needed to be here for the messy shit, as long as I got to see the end result.” Dean smiled as the blonde in the hospital bed carefully handed him the baby. The baby fussed until Dean had her safely in his arms.

“You’re still her uncle Dean, and my brother. You should have been here earlier,” The tall man scolded but looked fond of watching his brother with his baby.

“Your niece?” Castiel found himself speaking before he could stop himself knowing he was probably better off ignored. Everyone in the room turn towards him, noticing Cas for the first time. 

“Oh yeah,” Dean said staring at Cas, it seemed he forgot Cas was there too.

“And who are you?” A small blonde that stood near a red headed woman folded her arms across her chest, an eye brow raised at Cas.

“I’m Cas.” Castiel looked around the room nervously, to Castiel's surprise everyone had clear amused expressions. 

“You brought your one night stand to the birth of your niece?” An older woman that Castiel didn’t see before she spoke from the corner of the room. She had brown hair and a very distinctive New Yorker accent; maybe Brooklyn.

“That’s what I said!” Benny said bitterly, he seemed to be the only one in the room with a real problem that Cas was there.

“Looks like I’m not the only one having a baby tonight,” The blonde in the bed snickered.

“How old are you?” Dean's brother asked while eying Dean’s t-shirt that Castiel was wearing.

“I’m nineteen.” Castiel subconiously folded his arms over his chest beginning to feel uncomfortable by all the attention.

“God they get younger and younger,” The older woman smacked Dean on the head carefully, being mindful of the small baby in his arms.

Dean smirked at her, “An ass is an ass, no matter the age.”

“Gross!” Pretty much everyone in the room said.

“I mean legal of course. Consent and all that jazz.”

“Well anyway, my name his Ellen,” she walked over pulling Castiel into a hug, “Please do yourself a favor sweetie and stay away from men like Dean, you seem like such a nice boy.” Ellen turned toward the rest of the room but kept one arm around Castiel’s shoulders in a very protective motherly way.

“So let me introduce you to everyone since Dean is an asshole,” Ellen flipped Dean off, he gladly returned the gesture. Castiel thought it was sweet that Dean didn’t seem to want to put his new niece down.

“This tall class of water here is Sam, Dean’s brother and new father,” Ellen pointed to the tall man with long hair.

Sam smiled politely as Cas. Cas nodded back in acknowledgement.

“The small blonde is Jo, she’s my daughter, the woman next to her is her wife Charlie and you already know the assholes Dean and Benny.” Ellen turned her head towards Cas, “I’m Dean’s aunt by the way.”

“Nice to meet everybody,” he laughed nervously as everyone in the room had their attention on Castiel. It made him uneasy.

“No name yet?” Dean said to Jess and Sam but only looked at the baby Cas was grateful for Dean taking the attention off of him briefly, expect for Ellen who still had her arm around him. Castiel found the gesture oddly comforting.

“We can’t decide, we thought about Mary but she said she didn’t want us to name the baby after her. Middle name only.” Sam answered rubbing his wife’s shoulder.

“We’re open for suggestions,” Jess glared at the people around the room.

“You guys denied my name idea so I’m out,” Charlie pouted and folder her arms over her colorful star wars shirt.

“We’re not naming our daughter after an elf.” Sam rolled his eyes. Charlie glared and mumbled something inaudible to the room.

“What about Hael?” Everyone in the room snapped their heads towards Cas.

“Hael?” Jess gasped. “I love that!” She looked at Sam for conformation. Sam nodded his head and smiled at Cas.

“Hael means the angel of kindness," Cas offered awkwardly.

“Hael Mary Winchester,” Jess mumbled, “it sounds perfect.” She took Sam's hand in hers.

“You’re not seriously letting him name your kid are you?” Dean handed baby Hael over to Sam.

“It’s a beautiful name Dean, the best we've heard all day,” Jess smiled at Cas, “thank you for the suggestion Cas. Do you know someone named Hael?”

Cas hesitated, “I did, yeah.” Jess’ smile faltered slightly. She could tell there was a story there but was kind enough not to ask.

“It’s a good thing Dean brought you along, we wouldn’t have found a name so easily,” Sam nodded his head towards Cas.

“Everything happens for a reason I guess,” Cas shrugged. 

“Too true Cas, I believe in fate. Dean found you for a reason.” Charlie smiled sweetly at him.

“Jesus fucking christ Red, none of your hippie bullshit please.”

Cas cleared his throat, “Dean can I talk to you outside?” He asked, fearful Dean would say no.

“Uh sure,” It was the first time Cas had heard Dean sound so hesitant. 

Cas leaned against the hallway wall near Jess’ room. Dean stood unnaturally close to Cas, leaning on one shoulder, facing the teen.

“I can’t believe you made me wear a butt plug to the birth of your niece.” Castiel looked shellshocked staring at the wall opposite them.

Dean threw his head back in laughter, then bringing his face close to the side of Castiel’s neck, “Live a little kid.” He murmured against Castiel’s jaw. It made Castiel hot.

“Still very inappropriate Dean.” Castiel said quietly, wanting to pull away but also wanting to give in to Dean.

Dean chuckled before moving in front of Cas, placing both his hand on either side of Castiel’s head, tramping him against the wall. Dean moved his body closer, pressing his front against Castiel’s.

“We’re in public Dean,” Castiel glanced down the currently empty hallway.

“So?” Dean pressed impossibly closer, almost lifting Castiel off the floor with his body. Dean’s hands snaked around his middle, Castiel gripped Dean’s shoulders for support as Dean began nipping at his neck.

“Shit,” Cas whispered. The man was sexy, and Castiel was a teenager, a very horny teenager with very little experience. It didn’t take long for Cas to become hard in his jeans.

“Hm. Very responsive,” Dean rutted his hips against Castiel’s. “I bet I could make you come again, just like this.” Dean licked a long stripe up Castiel’s neck. Landing to nibble at his ear. Dean rocked his hips against Castiel in very small, tight movements, that seemed barely noticeable to anyone else, but _very_ noticeable to Cas.

“Damn Dean, please don’t make me come here.” Castiel whined. It seemed Dean was out to embarrass Castiel. Cas had little to no experience in the sex area, and now he was being dry humped in a very public place with the man’s family just behind the wall he was pressed against. It seemed evil.

“You don’t want to come?” Dean mouthed along Castiel’s jaw. Pulling his head away briefly to look down the hallway. “There’s a nurse down there.” Castiel turned to his to watch the nurse going in and out of rooms. She seemed too busy to notice Dean and Cas.

“I’ll make you come before she gets to Jess’ room.” Dean pressed a hard kiss against Castiel’s mouth, his hips moving rougher against him. Cas moaned against Dean’s mouth, he could feel the burn in his abdomen.

“I-I’m close Dean,” Castiel breathed against Dean’s lips. Dean hummed reaching one hand down to cup Castiel’s ass, the movement shifting the plug in Castiel’s ass causing a loud groan from his mouth.

Dean quickly placed his lips onto Castiel’s trying to quiet him. With a few more quick thrust Castiel was coming in his jeans. “Shit, shit, shit,” Castiel clenched onto Dean’s shoulders, his hips twitching from his orgasm.

“That was pretty hot Cas,” Dean pulled away slightly, letting Castiel breathe. If Castiel hadn’t been so red faced and embarrassed he would have been elated that Dean finally remembered his name.

Cas put his hands over his face, “I can’t believe that just happened.” Castiel wasn’t sure if he was embarrassed by the public sex and that the nurse down the hall _definitely_ saw them, or by how fast he actually came. Dean barely got a hard on while Castiel was coming. 

“There’s a bathroom right there, you should clean yourself up,” Dean looked down at the wet spot in Castiel’s jeans. “Good thing my shirt is big on you, you can cover up the wet spot.”

Dean smirked and cupped his hands around Castiel’s jaw leaning in giving Castiel a slow kiss, his tongue explorative, a kiss Castiel could finally keep up with.

“Dean Winchester!” Dean pulled away and rolled his eyes at the woman’s voice. Castiel’s eyes widened in panic.

Dean turned towards the source of the noise.

“Hey Mom.”


	4. Chapter 4

“Hey Mom.”

Dean walked over to an older woman and Cas was slightly shocked by her appearance. The woman Dean was hugging and called Mom was beautiful, Cas thought she looked just like Dean. She might've been blonde at one point in her life and tanned like Dean, but the woman standing the hallway was pale with a blue bandana tied around her head and it was clear to Castiel that she had no hair. Dean's mom obviously had cancer.

“Who is your friend Dean?” She had a small playful smile that was so similar to Dean's.

“Oh uh, this is Cas.” Castiel tugged on the shirt he was wearing, trying to cover the wet spot. “And Cas, this is my Mom.” It was the first time that night Cas had seen Dean's confidence falter even slightly. 

“I’m Mary,” Mary stuck out her hand for Cas to shake, her hand was small and cold she seemed breakable, even to Cas.

“Nice to meet you.” Mary took in Castiel in for a moment, studying him she smiled when she noticed Dean's t-shirt.

“You didn’t tell me you were dating anyone.” Mary eye’d her son.

“Cause I’m not. Cas-He’s just a-“ Dean shrugged shamefully.

Mary sighed, “Odd you don't usually bring your one night stands to meet the family.” Mary quirked an eyebrow in a way that reminded Cas of his own mother.

“Yeah I’m starting to realize the mistake,” Dean sighed heavily, shooting an almost apologetic glance at Castiel.

“You going inside Mom?”

“Just to say hello to everyone, then I’ll be out in the waiting room. I shouldn’t be standing too long.” Something flashed across Dean’s face; a sad expression that made him look so different.

“I should wait in the waiting room as well actually,” Dean looked at Cas suddenly, “Or maybe I should just go.”

Dean shook his head, “Not with my shirt you’re not. You thief,” Dean glared playfully, “I won't be too much longer, you can wait." Dean ordered, Dean's bossiness was almost starting to piss Cas off. 

The anger feeling quickly faded to giddiness when Castiel realized Dean wanted him to stay. Dean _wanted_ Cas.

After Dean and his mother disappeared back into Jess’ room Cas quickly scrambled into the bathroom.

Cas peeled off his tight pants and underwear letting them pool at his knees, he did the best he could to clean up his own semen. A moment of rebellion coursed through Castiel’s veins. He reached between his legs feeling around until he found the end of Dean’s butt plug. Cas panted as he wiggled it out of him, sighing in relief as he held it in his hand.

If Dean wanted to embarrassed Cas publicly like he did, then Cas wasn’t going to completely submit to the older man. Cas threw the purple plug into the trash while grinning evilly, he wiped his ass of any extra lube and pulled up his pants.

He knew Dean would be pissed that Cas not only took the butt plug out but threw it away. “Good.” Cas murmured to himself. Dean deserved a little defiance.

* * *

 

Castiel sat in the waiting room of the labor/delivery floor of the hostpial, a constant nagging in the back of his mind telling him he should leave and take a bus to Meg’s house, but if Dean really wanted him gone Cas knew the man would just say so.

The blue eyed teen jumped when someone sat next to him suddenly. He turned to see Dean’s mother smiling politely. “Hello dear.” She greeted.

“Hi.” Cas started out awkwardly then there was a pause and Cas couldn't help but ask, “What’s wrong with you? Do you have cancer?” Cas blurted out. 

Mary chuckled, “Yes as a matter of fact, I do.” She raised an eyebrow at Cas, “It started out as breast cancer, I had it years ago I won the battle but it only came back with avenges. It’s in my bones now.” She looked away sadly.

“I’m sorry, I shouldn’t have asked like that, it was very rude of me.”

“It’s okay dear.” She turned her body to fully face Cas, “They told me about you naming Hael. Where’d the name come from?”

Cas hesitated, “Hael was my sister.” Cas was feeling less guilty about being so noisy towards Mary, she seemed equally noisy.

“Was?” Mary questioned. Cas never openly told anyone about his sister before. He kept Hael as a distant memory.

“I was an accident,” Cas sighed and Mary smirked, she knew she was going to get him to talk. “All my siblings are a lot older then me. I guess my parents felt bad that I didn’t have someone to play with, when you grow up as rich as my family all you really have is each other.” Cas explained and Mary nodded her head, listening intently.

“Since my mom couldn’t physically carry anymore children my parents paid for a surrogate. I was four years old when Hael was born.” Cas paused and frowned at the white titled floor.

“Go on.” Mary encouraged.

“In Jersey there was a lake behind our house, in winter it froze over but we were never allowed to go on the ice. It was too thin and dangerous.” Cas started mumbled.

Mary nodded, she seemed to understand where the story was going. Cas continued anyway, “I was ten and she was six years old. I-It was my fault.”

“I doubt it was your fault, you were a child.” Mary offered sweetly.

Cas looked Mary in the eye and frowned, “I dared her to wonder onto the ice and she did it and she fell, and I was too scared to save her. How is that not my fault?”

“I’m so sorry,” was all it seemed Mary could say. Cas shook his head, angry that he just shared so much to a stranger but Mary seemed opened and warm unlike his own mother who was closed off and cold.

“My parents never forgave me for that. Living with them is a nightmare, my mom dotes on me but not in the way a loving parent would. It’s more controlling.” Cas wished he would stop sharing his soul with this woman.

“You still live with them?” Mary questioned without judgment.

“Yeah, they pay for my schooling and-“ Cas shrugged, “They own me financially, I couldn’t make it without them.”

“You should work at our diner.” Mary offered with a weak smile.

“Diner?” Cas titled his head.

“Yeah, my sister-in-law Ellen,” Cas nodded in understanding, she was the loud mouth women he had met earlier, “We own a diner together. It’s called Roadhouse and I’ve been getting too weak to work there anymore. They’ll need a new server. You should try it out, make some money of your own.”

It didn’t sound like a bad idea, Cas loved the thought of being able to earn his out keep and leave his parents nest. Cas was also realistic and knew a waiter salary wouldn’t pay for anything in New York City. Cas wasn't sure if he could juggle school and a job but maybe that was his rich kid privilege speaking. Since Cas was a senior he only had half days at school, it was possible.

Before Cas could answer the door to the waiting room opened and Ellen walked in with her daughter. Cas couldn't remember the blondes named but remembered she was married to that red headed woman.

“Ellen, I’m glad you’re here.” Mary smiled as Ellen took a seat across from them. “I was just speaking with Cas here about taking my place at the diner.”

Ellen raised her eyebrows in surprise, “You really think it’s time for you-“ Ellen glanced at her daughter, the blonde wore a worried expression.

“I do think it’s time Ellen,” Mary nodded sadly.

“Well then,” She looked at Cas, “What do you think, boy?”

“I uh, this is awfully nice of all of you but I’ve never worked before..”

“I have an amazing judge of character Cas, I think you’ll do well.” Ellen encouraged.

“If you want some freedom from your parents, I think you should do it.” Mary patted his knee.

“I go to school Monday through Friday from eight act to noon.”

Ellen nodded, “You can work weekends or evenings if you’d like; part time maybe four days a week?”

“Okay, I think I can handle that,” Cas smiled, his first job. Something he gets to do on his own without his parents suffocating him. “And Mary if you mind, please don’t say anything about what I’ve told you tonight. I’m not sure why I spoke so openly with you-”

Mary nodded, “I won’t say a word Cas.”

Cas and Ellen went over logistics of his new job. Cas reassured Ellen that he had transportation, he didn’t exactly tell that his transportation was his own driver, a lie about the subway would have to do.

"So you're ready to start Saturday morning then?" Ellen was typing something in her phone.

"Yes, I can." Cas nodded in excitement, "Thank you for the the offer and giving me a chance."

"It's not a problem," Ellen looked at Mary, "He's going to need a nickname."

Mary looked at Cas in thought, "I'm sure it will come to us."

"A nickname?" 

"Oh yes, everyone who works at the diner gets a nickname for their name tag. No one uses their real names." The young blonde said. "I'm Watson. When Charlie worked there she was Holmes so our nicknames made more sense," she chuckled. 

"I'm Boss, or Boss Lady." Ellen said proudly.

"Or just Bossy," Ellen's daughter mumbled, receiving a hard glare from her mother.

"I was Huntress." Mary smiled at Cas. 

"We'll think of something for you." 

Cas couldn't wait to receive a nickname. Dean's family was giving Castiel something he had always longed for, a sense of belonging. The teen went out that night just looking to _lose_ his virginity, but it became apparent to him that he may have actually _found_ something.


	5. Chapter 5

Dean would never admit this verbally because he liked to keep his _happy_   _emotions_ in check, but the man was completely in love with his new baby niece. Dean could however verbalize his strong dislike that Twink (of all people) got to name her.

Dean wasn’t particularly worried that every time he used his niece’s name he would think about Twink or worry that the kid might stick around, Twink was someone Dean knew he could get rid of easily; mentally and physically. Dean forgot people easily, it was simply part of his nature - they never stayed and he never cared. So Twink getting to name his perfect baby niece was simply a current frustration that he would have to take out on Twink’s ass later.

The moment Dean realized that Mary, Ellen and Jo were all missing from Jess’ room was the moment he knew it was time to say goodbye to baby Hael and seek out his conquest. The thought that Twink might be somewhere alone with his mother, aunt and cousin made Dean panic and forced him to practically run towards the waiting room. He just needed to get the both of them far away from his family, getting the twink home and fuck him senseless was all he wanted to do now. Dean was starting to feel pent up, off balance and _hungry_.

Upon entering the labor/delivery waiting room Mary, Ellen and Jo were all hysterically laughing, clearly at something Twink said, the teen had this smug smirk like he had just wooed an impossible crowd. Dean didn’t like it.

“Hey!” All heads snapped towards Dean, but Dean was only really speaking to one person, “Let’s go.” Dean gestured quickly towards the door, the quicker they got out of there the better.

Twink nodded and turned his attention back to Dean’s family, “It was really great meeting all of you.” He smiled and gave Mary a quick hug. Dean huffed in annoyance, not doing anything to hide his strong dislike toward the current situation.

“Take care of yourself Castiel! We’ll be seeing you.” Ellen shook Twink’s hand and Dean furrowed his eyebrows in confusion, like hell Ellen would be seeing Twink again. Twink most likely lived near the university and if Dean had any luck at all (which he did), Twink would stay on his own hollowed grounds and never come near the upper west side again.

“Hurry Cas.” Dean rolled his eyes, a quick slip of Twink’s name left Dean’s tongue. For some reason his name had stuck but Dean knew by tomorrow the name would be gone; the names, just like the men, never stuck around. And Dean loved it that way. It was easy that way.

Jo and Charlie promised to take Benny home which was a huge sigh of relief for Dean.The last thing he wanted was an extra ten minute drive to Benny’s brownstone.

Dean wasn’t overly surprised that Twink talked the entire way back to the apartment but Dean was more then happy to block out most of the kids ramblings only catching a few things here and there, enough to give one worded responses to.

The second the elevator to Dean’s penthouse dinged the older man was all over Cas with no rejection from the teen. Dean eagerly grabbed two handfuls of twink ass pulling him close to devour his hot mouth. The older man vigorously tongue fucked the inners of Twink’s mouth causing happy little hums from the younger man.

It was obvious to Dean that at Twink’s young age of nineteen he wasn’t too experienced sexually and it had definitely showed in the lack in Twink’s technique. As Dean dragged Twink up the stairs and into his bedroom it briefly crossed Dean’s mind that Twink might be a virgin, and honestly he was too scared to ask if he was. Dean had an important rule not to ever fuck a virgin, they were clingy and a man always remembers his first fuck - Dean never wanted to be that person for someone. If Twink were a virgin, Dean knew he would ignore his rule and he would be that person for him. That wasn’t something he was willingly to acknowledge at his current state of arousal.

Dean pushed Twink away once they were in his bedroom, “Undress.” He ordered taking in Twink’s face, his blue eyes were wild with lust, his mouth shiny and plump. Dean licked his lips at the sight, he felt a new sexual awakening just looking at the teen, he wanted to wreck him in the best possible way.

* * *

Dean was pissed, _more_ then pissed about the missing butt plug in Castiel’s ass. After Dean discovered the lack of toy in his ass, he forced the teen on all fours in the middle of his bed. Dean thought two smacks to each ass cheek was punishment enough, Dean chuckled at Cas when he realized the spankings weren’t really punishments at all.

“You liked that huh?” Dean nipped at Castiel’s pink butt cheek. Castiel bit his lip, willingly himself not to respond.

“So that’s how I get you to shut up? Good to know.” Dean ran both hands over Castiel’s ass and spread his cheeks. Castiel’s face flushed, slightly embarrassed by being so exposed, after a few pauses he wondered what Dean was planning, the teen certainly didn’t expect to feel the stroke of Dean’s wet tongue over his hole.

Cas clenched and unexpectedly moaned in approval. He might’ve been a virgin but he knew what a rim job was, he’d seen it in porn many times it was however safe to say that Cas wasn’t expecting to get one tonight.

Cas fell onto his elbows grinding his ass into Dean’s face. Dean showed appreciation by sucking at his entrance, swirling his talented tongue around the outside then pointing it to loosen Cas up.

“Oh god,” Castiel moaned, gripping at Dean’s sheets as the older man’s tongue worked itself into Cas. Dean gripped Cas’ ass harder as he roughly tongue fucked him. With one last broad stroke of tongue Dean pulled away and Cas whined at the loss wondering how anything could compare to that glorious feeling.

“You’re still pretty loose,” Dean gripped Castiel’s hips easily flipping him over onto his back. “However, I am still pissed at you.” Dean cupped Castiel’s balls causing him to arch his back.

“Then do something about it.” Cas finally found his voice and put it to good use. Dean chuckled and quirked an eyebrow.

“Oh I plan to.” Dean eyed Castiel’s erection, removing his hand from Cas’ balls to run his thumb over the head of Cas’ cock, “Fuck you’re all wet from just a little ass play and kissing? So glad I picked you for tonight Twink.”

Before Castiel registered what he was doing his hand flew grabbing at Dean’s wrist pulling it away from his cock. “Use my real name or I’m leaving. Don’t think I won’t.” Castiel challenged with a hard glare.

After the brief look of shock washed off of Dean’s face he threw his head back in laughter. “Well shit Cas, I think I like you.”

Cas smirked and released his grip on Dean’s wrist. Dean leaned his head down flicking his tongue over Cas’ wet cock head lapping up the precome gathered there. Cas’s hips twitched at the maneuver, he was beginning to feel embarrassingly needy, and by Dean’s cocky grin the other man knew it.

With a smug smirk Dean draped his body over Cas’, lining their erections and rolling his hips at a teasing pace. Cas panted grabbing the back of Dean’s neck, pulling him down into the sweet, slow kiss he had been wanting to give Dean all night. The whole night Dean had been all tongue and teeth, Cas wanted something softer — so he took it. Much to Castiel’s surprise Dean let him control the kiss as he kept his hips moving in small circles nipping almost affectionately at Cas’ bottom lip. Cas took pleasure in being the one to sweep his tongue in, claiming Dean’s mouth with slow thrusts.

Dean moaned before forcing his head away and sitting up on his knees between Cas’ open thighs, “Enough of that,” A dominate quirk of Dean’s eyebrow made the burn in Cas’ stomach even more, “We have other matters to attend to.” Dean grabbed the lube and condom he had already placed on the bed.

Just before Dean turned Cas back over onto his knees the teen spoke, “You don’t need to use the condom,” Castiel wanted the full experience for his first time, he heard barebacking felt better then sex with a condom. Sure it was messier, but Cas wanted that.

Dean frowned at him, “Listen to me, you never fuck anyone without a condom,” he said angrily, “Especially a stranger, haven’t you heard of aids?”

“I- yes but- I trust you Dean.” Cas could feel his naivety showing.

“Don’t ever trust anyone you don’t know to fuck you bare. Damn Cas, looking like you do and asking for a bareback fuck, most men wouldn’t hesitate. You could end up dead, don’t be stupid.” Dean tore the condom packet open with his teeth, that at least gave Cas hope that they were still going to have sex.

“Alright, sorry.” Cas mumbled in submission. Dean was right after all and Cas knew that.

“Don’t be sorry, just learn from what I told you and don’t make mistakes again.” Dean poured lube onto his fingers and rubbed them against Castiel’s entrance before slowly pushing two fingers in.

Dean leaned over Cas, “Promise you won’t ever have sex with a stranger without a condom again,” he whispered, spreading his two fingers, scissoring Cas’ already loosened hole. Cas figured Dean thought the teen had asked for that before from men, Dean didn’t know it was his first time.

It took a moment for Cas a to register that Dean was waiting for an answer from him, “O-oh yes I promise,” Cas moaned, gripping Dean’s shoulders, “Oh shit,” he rocked his hips against Dean’s fingers searching for that feeling again. Cas knew Dean found his prostate, the teen had fingered himself a couple of times before and knew what that feeling was but it felt a million times better when Dean brushed against it.

“Good boy,” Dean practically purred. Dean removed his fingers much to Cas’ distain.

Cas stared at Dean then at his latex covered cock. He swallowed the lump in his throat, the sudden serge of nervousness made his erection flag slightly. As Cas innerly panicked, he tried his hardest not to show just how scared he was of this moment. A moment he had thought about a lot but still needed to brace himself for. He was about to be fucked by a much older man that Cas would gladly label a sex god.

Dean hesitated and Cas cringed, he knew in that moment that Dean noticed his brief panic.

“You’re a virgin, aren't you?” Dean asked seriously.

“Y-yes.” There was no sense in lying about it. Cas placed his hands over his face, out of embarrassment and not really wanting to see Dean’s reaction. He knew he should’ve been honest, but with Dean’s experience he also felt Dean should’ve figured it out — obviously he had.

“Hm,” Dean sounded thoughtful. Warm hands gripped Cas’ wrist pulling them away from his reddened face. Dean’s lips replaced his hands immediately, placing small reassuring kisses along Cas’ cheek bone and jaw. Once Cas relaxed Dean’s mouth moved to his, the older man indulging Cas in a sensual kiss, it was Cas’ favorite kiss he’s received thus far and it ended with Dean playfully tugging at Cas’ bottom lip, they both smiled and Cas was much happier with the more relaxed atmosphere. He wasn’t sure how or what Dean did, but he once again thanked whatever god had sent Dean his way that night.

“I want you on your knees; bowing.” Dean moved slow, helping Cas get comfortable on his knees, his chest pressed into a pillow Dean gave him to hold onto. He froze momentarily, completely unsure how to ask Dean he would rather be on his back, looking at the older man.

A hand ran down his back, Dean’s fingers carefully tracing over Cas’ entrance, “Dean,” Cas moaned, uncaring how needy he sounded.

“I got you,” Cas felt Dean shift behind him, “This position is better for your first time,” Dean’s draped his body over Cas’ back mumbling into his ear, “If you want to switch it up later, just tell me.” Cas nodded his head gratefully and with a brief brush of lips against his ear Dean gently pressed his cock head against Cas’ entrance, he pressed and pressed until Cas’ body finally gave way and Dean sunk into him.

Cas groaned, gripping Dean’s pillow and bitting it to quiet himself. It wasn’t the slight stab of pain of being stretched that brought some tears to Cas’ eyes, it was the genteelness of Dean. Dean rubbed his hands over his lower back, relaxing him as he slowly entered Cas. The teen hadn't expected any kind of carefulness with Dean, but Dean made himself feel special, like Cas was something precious.

* * *

Dean was surprised by the ease Cas’ body gave as he bottomed out, for Cas’ first time he was expecting some resistance, he wondered if Cas had ever fucked himself with a dildo, the thought drove Dean to pull back with a slow shallow thrust probably before Cas was really ready for it. He knew he needed to give Cas time to adjust but the heat surrounding him felt too good. Cas grunted at the sudden thrust, then Dean took his pause — slowing his breathing down running his hands up and down the planes of Cas’ back.

This didn’t happen often to Dean, but maybe once every two years Dean gets ahold of something special. A fuck that’s just different from the rest, ones he likes to take his time with. Cas was different, Cas was different from all those other different’s. Cas looked, felt and sounded perfect - he wasn’t like the other twink’s he’d fucked in the past, the loud slutty sounding men. Cas was patient and quiet, he was pure. Dean felt a twinge of guilt, because Cas _was_ pure, and Dean was ruining him.

Cas shifted beneath him, turning his head to the side like he was trying to look at Dean.

“Are you okay?” Dean needed to ask as he bent to nuzzle the back of Cas’ neck. He felt Cas nodded but the teen was still tense.

“Relax.” Dean whispered to Cas while pecking kisses down his spine. Dean could feel Cas slowly melt into relaxation, his ass clenching tighter around his cock, “Hmm, good.” Dean moaned.

“Please-“ Cas whimpered. Automatically Dean wanted to start moving, to start pounding into the teen’s virgin ass but please, that could easily mean _please stop_ , and Dean wasn’t going to allow that misunderstanding.

“Please what Cas? Talk to me,” Dean’s hands desperately held Cas’ hips, just waiting for the consent he needed.

“Please move, I-I want more please Dean.” Cas begged, his voice muffled by the pillow under him.

“Fuck, you sound pretty when you beg like that.” Dean pushed Cas’ ass cheeks apart with his hands, looking down, watching himself as he slowly dragged himself half way out of Cas before slowly pushing back in. Dean moaned at the sight - his cock shiny from the condom and lube with Cas’ tight hole stretching around him. Everything was perfect. Cas’ hips twitched with a low moan and Dean knew, he knew Cas was ready to fucked.

Cas’ ring automatically contracted trying to prevent Dean from moving but he was insistent and the heat of finally getting to fuck Cas took over — slowly at first, then increased in tempo listening to Cas’ noises, Dean’s hips constantly responding to his string of moans.

Dean knew what he was doing, he knew where to hit and how hard to hit it. It took maybe five minutes of fucking Cas to find what he was looking for and the moment his cock head hit Cas’ prostate the kid was done. Cas was wiggling around and moving non stop in a way that really showed he was a virgin. Cas was good a taking a cock, but he wasn’t too good at being fucked yet. It was new to him and now Dean knew that.

“Stop,” Cas had said for the third time but it was Dean’s first time hearing it, he stopped his steady thrust.

“I need-“ Cas was breathing heavily from the recent assault on his ass and Dean wasn’t sure if the teen was actually enjoying himself, but he sure as fuck sounded like he was.

“What Cas?” Dean pulled out of Cas with a sad whine from the bottom boy.

On shaky arms Cas flipped himself onto his back. Dean took in the marvelous sight below him. Cas’ face was completely flushed pink, a thick line of sweat gathered at his forehead, the teens smooth cock was leaking with the head turning purple from pleasure and the need to release.

“Fuck you look amazing,” Dean mumbled, and the flush from Cas’ face moved down his chest.

“Like this, please,” Dean almost nutted in the condom from the sound of the teens whiny, needy voice his lower lip jutting out in a pout. It almost killed Dean, but what a way to go out.

Dean gripped the back of Cas’ knees and pushed them to his chest, “Hold your knees up.” He instructed with a shockingly calm voice. Cas moved quickly, not only pulling his knees to his chest but spreading his legs wider — and fuck was he flexible.

“Needy.” Dean couldn’t help the petty jab before lining himself up, inserting himself fully into Cas once again.

“Ohh fuck,” Cas let out a shaky breath, arching his back almost completely off the bed.

Dean fell forward so the two were chest to chest, he snuck his arms under Cas’ shoulders holding him tightly to prevent Cas from moving too much. Dean felt Cas release his own legs, grabbing onto Dean’s back quickly from the sudden movement. Cas’ legs wrapped around Dean’s middle easily as he hooked his ankles together.

Dean could feel Cas’ cock trapped between them and he wondered if he could get Cas to come just like this. No hands. Just friction of their bodies.

Dean began moving again, Cas’ groan was muffled by Dean’s neck. Dean set a slow deep thrust, circling his hips causing Cas to bite lightly at the side of Dean’s neck and Dean was in heaven.

“Oh fuck you feel so good,” Dean groaned while continuing to rolling his hips with purpose.

“Dean!” Cas gasped and dug his fingernails into Dean’s back and another sharp bite but this time to Dean’s shoulder. Dean prayed there would be marks in the morning, he wanted Cas’ imprint to last a couple of days, that feeling was very new to him.

Dean began to feel the familiar burn and it was all happening too soon, he paused his movement to sit up on his knees. Cas looked even more of a wreck below him, Dean made sure to snap a mental picture for a rainy day because fuck Twink was beautiful like that and Dean loved appreciating beautiful things.

“Dean please,” Cas whined desperately circling his hips trying to fuck himself on Dean’s cock.

Dean smiled gripping Cas by the hips, “I got you.” Dean growled pulling back and snapping his hips harder then he did before, making sure to hit that spot to make Cas lose it fast.

“Oh god,” Cas arched his back letting his hands reaching above him, bracing himself against the headboard to prevent from moving up while Dean fucked him harder, his previous rhythm was losing control as he drew closer to coming.

“Damn Cas,” Dean licked his lips at the sight below him, he wanted to do so many things to Cas all at the same time. But he had a fuck once rule, and he wasn’t letting this sexy virgin twink ruin it.

“Touch yourself,” Dean sped up his thrust, he was so close and knew Cas was right there on the edge with him. They were going to come together if it was the last thing Dean did.

Cas’ right hand moved from the headboard and wrapped around his cock. Cas kept moaning as his hand worked itself up and down his shaft.

“That’s it, cum for me Cas.”

* * *

Cas was positive he had blacked out, the built up pleasure of Dean slamming into him, skillfully hitting his prostate with each stroke mixed with Dean’s words of encouragement gave Cas a light headedness he had never felt before.

As Cas came back around at first all he felt was Dean pressing light kisses along his neck and jaw. He might’ve been mumbling something but Cas wasn’t too sure what it was. The teen tried to wiggle his body around, but realizing he couldn’t move too much with Dean laying over him.

“You back?” Dean’s amused voice finally broke whatever sound barrier Cas had up.

“Yes,” Cas cleared his throat as his voice cracked. He closed his eyes as Dean pulled away from him and moved off the bed. Cas wasn't sure what Dean was doing but he wanted to bask in his after glow a little while longer, Cas feared briefly that Dean was going to kick him out straight away.

The teen jumped when he felt a warm cloth move over his stomach, he opened his eyes to an overly satisfied Dean cleaning the come off his stomach. Cas felt a twinge of disappointment he blacked out and missed Dean’s orgasm. Something he would’ve wanted to see. Dean didn’t say anything and Cas didn’t either. Words weren’t needed, but that’s when everything sunk in, Cas just had sex. He finally lost his virginity and it was probably the most amazing experience of his life and he wanted more. He wanted Dean to own him, to take him in whatever way he wanted.

“What are you smiling about?” Dean asked moving onto the bed besides Cas, reaching down and pulling the sheet pooled at the end of the bed and lifting it over their naked bodies.

“Thank you Dean.” Cas said softly.

“Um, you’re welcome?” Dean clapped his hands twice, resulting the lights in the bedroom to turn off. The sudden sounds made Cas jump, which in return made Dean laugh.

“No really, thank you. You’ve been… Very nice and careful with me.” Cas’ sincerity only seemed to annoy Dean.

“It’s fine Cas,” Cas could practically hear the eye roll.

“Was everything good for you?” It was late and Cas knew Dean probably wanted to sleep but Cas felt wide awake.

Dean snickered, “Yeah Cas you were great. How was everything for you?” Cas could hear the sarcasm but answered anyway.

“It was amazing, actually.”

Cas laid on his back and wondered if Dean would be opposed to post sex cuddling, he didn’t seem the type but Cas definitely was. Cas stiffened when he felt Dean start to move next to him. A sudden touch on Cas’ arm made him jump. “God you’re jumpy. I’m not going to hurt you.” Dean murmured as he man handled Cas so he was laying on his side with his back to Dean’s.

“I know you won’t.” Cas said with confidence. He smiled when he realized what Dean was doing. Dean slotted himself close behind Cas and threw an arm around his middle. Cas relaxed against the older mans chest. He wondered if Dean could read minds or if he accidentally voiced his need to cuddle out loud.

“You said it out loud.” Dean chuckled, Cas could feel the puffs of air on the back of his neck.

“Oh. I do that sometimes, say things when I think I’m just saying them in my head.” Cas couldn’t feel embarrassed about it, Dean was spooning him and he felt over joyed by the moment.

“I’m not surprised,” Dean sounded sleepy but amused. “Go to sleep now Cas,” Dean whispered into his hair and Cas wondered if Dean could psychically feel his happy vibrations.

It didn’t take Cas long to fall asleep in Dean’s arms. Tomorrow he’d have the deal with getting to school and possibly having to reveal to Dean the truth about his age.

**Notes for the Chapter:**

> 1\. Notice the added tags. There might be more added later.  
> 2\. I gave up on chapter titles already lol.  
> 3\. I'll update now officially every two weeks, either Tuesday or Wednesday.


	6. Chapter 6

Dean regretted the moment he woke up and opened his eyes. Last night he made mistakes - mistakes he had never made before. Dean could feel the tight knot in his chest as Cas laid curled at his side and the sun rose filling his apartment with light.

The way Dean had chosen to live his life, he needed guide lines to keep himself ( _and not so little Dean_ ) in check. Dean had lived by these guide lines for years and Twink just came along to fuck up his good run. Dean shut his eyes again mentally going through his list of rules.

_Never learn their name._   
_Never let them meet the family._   
_Never let them stay the night._   
_Never fuck them twice._   
_Never cuddle._   
_Never, ever fuck a virgin._   
_Never give your phone number._   
_Never fall in love._

He was five out of eight, knee deep in mistakes. Dean sighed heavily with remorse and looked down almost fondly at the mop of dark brown hair on his chest. They fell asleep spooning but at some point in the night Cas ended curled up on Dean’s chest like a house cat, and it felt… _nice_. Dean took to blaming the birth of his niece for his indiscretions and weakness. Dean wasn’t sure what it was but he felt an unbelievable urge to coddle Cas, whatever it was he hoped the feeling left him once Cas did. He couldn’t have another night of fuck ups, he couldn’t handle another Alastair, Dean growled at the thought of his ex — _his hell years_.

Dean slipped away from the warmth of Cas to sit up on the edge of the bed. “Dean?” a small sleepy croak from behind him. Dean looked over his shoulder and regretted the moment he did, Cas pushed himself onto his elbow his other hand absentmindedly running through his unruly hair. He looked perfect, Dean’s cock jumped as his heart plummeted towards his stomach. He wanted nothing more then to pin Cas down and indulge in amazing, lazy morning sex. But that was another rule.

“What time is it?” Cas adorably yawned and Dean wanted to kick him to the curb.

Dean cleared his throat and glanced at his phone, “6:15 am.”

Cas scrunched up his face making Dean chuckle, “My body is on an automatic clock, this is the time I wake up for work.”

Cas collapsed onto his back, “Me too, I have to be to school by eight.” Cas groaned.

Dean frowned, “Sorry man, you aren’t making it all the way to NYU by eight. Not with morning New York traffic.”

“I uh, I can be late. I take the subway.” Cas said roboticly, almost like he had rehearsed the answer. Before Dean could think any more about it Cas asked if he could use his shower. Dean wanted to say no, really he did. Dean told Cas where the towels were and unashamedly watched his naked ass disappear into his bathroom.

* * *

It took Cas a sold four minutes to figure out Dean’s high-tech shower system. Honestly Cas lived in a much more expensive apartment but everything was old school, the way his parents liked it.

Cas sighed tipping his head back and rolling his shoulders under the warm water. He felt sore, especially between his legs, but he was young and he would bounce back fast.

A small smile played on his lips thinking about the night before. It had been such an sensational experience for the normally very sheltered teen, Cas wasn't sure how to go back to normal now.

A sudden chill on Cas’ back side made the teen open his eyes, landing immediately on Dean a very naked and half hard Dean opening the glass shower door and stepping in crowding Cas under the water to wet his hair.

Dean shot him a cocky smirk before nipping playfully at Cas’ jaw while reaching behind the teen for the shampoo.

Cas wasn’t sure what to think about Dean turning him around and washing his hair for him, his thick fingers messaging Cas’ scalp delicately made the teen moan - _Did Dean do this with everybody_? He didn’t seem the type. But Dean was full of surprises and Cas loved being surprised.

Dean moved Cas under the water to rinse his hair out, his hands caressing the back of Castiel's neck. Dean still hadn’t said a word, but Cas was in heaven with all the attention he didn’t mind the silence.

“So you uh work today?” Cas tried ask casually.

“Mhmm,” Dean answered.

Dean still didn't say anything as he moved for the body wash and Cas was really beginning to wonder what Dean was thinking. The older man was an enigma, sometimes a disengaged asshole, other times very tentative and sweet - Like now. 

All thoughts were cut off by Dean’s soapy hands traveling up and down his chest. Cas’ cock twitched as Dean rubbed his slippery thumbs over his hardened nipples.

“Dean,” Cas groaned, unsure of Dean intentions with the intimate shower.

Dean smirked and press a quick kiss to the corner of Cas’ mouth before kneeling in front of him to soap up his legs. Dean’s hands messaged Castiel's thighs all the way down to his ankles, his face inches away from Cas’ hardening member. Dean never moved toward Cas’ cock, both his hands and mouth completely avoiding his semi.

“Dean-“ Cas whined and pumped his hips towards Dean’s face. Dean looked up at Cas as he was rubbing his hands up and down Cas’ inner thighs. He smiled and nipped at Cas’ hip bone, Cas but his lip, he could feel the heat of Dean’s body near the place that was so desperate for attention.

* * *

Dean was being selfish, he was allowing himself to indulge with Cas. Sex was off the table, _because rules_ , but he had no problem touching and as much as Dean wanted to get Cas into his mouth, slowly unwinding him in the shower was too much fun. Cas’ cheek’s were pink, his wet hair plastered to his forehead - Dean thought he looked younger this way. He looked innocent until he moaned like a porn star as Dean placed open mouthed kissed along his hipbone and lower stomach. Never intentionally touching Cas’ dick but his erection brushed against Dean a few times and Cas would jerk his hips looking for friction.

Dean slowly dragged his hands from the inners of Cas’ thigh up to message his balls, running his hands around messaging Cas’ pubic area. Dean noticed last night that Cas didn’t have pubic hair, but the area was rough and recently shaved.

“You shave your pubes?” Dean asked a wrecked and unresponsive Cas. Dean watched Cas’ dick twitch with a bead of pre come leaking out.

“I-uh- yeah,” Cas was whining. Dean loved it.

“Why?” Dean asked as he pulled away from the assault on Cas’ hipbones and Cas seemed to take a minutes for his brain to catch up.

“I thought that’s what guys would like,” He said shyly looking down at Dean through his eyelashes and it was Dean’s turn to whine.

“Hm. I think trimming and just some mancasping is good enough. No pubes makes you seem like jailbait. No man likes to feel like a paedophile… well I guess some actually do.” Dean half joked but also offered the advice, the comment made Cas look off away from Dean.

“Please Dean,” Cas whispered and but his lip and Dean gave in almost immediately.

Dean started sucking Cas’ semi-hard dick, and within seconds he was fully hard and so was Dean. Dean took all of Cas into his mouth and started bobbing his head faster while one hand started rubbing Cas’ ass and with the other rubbing his chest and nipples.

Dean pulled of with a pop then started sucking Cas’ balls, putting one in and then the other, Cas threw his head back and moaned in approval. Dean went back to sucking his dick faster and faster. He knew Cas was close, he could taste the constant pre come leaking out of the teen.

”Hmmm, yeah-” Cas moaned in pure delight. Dean hummed as he deep throated Cas in response.

"I'm gonna cum Dean" he moaned loudly, gripping Dean’s hair harder as he lost control. Dean kept going, sucking hard and bobbing fast until Cas’ dick exploded with cum right in his mouth.

Dean moved away and swallowed all of Cas "Your cum tastes good,” Dean’s voice was rough from having a dick probing the back of his throat.

Dean sucked a bruise into Cas’ hipbone, thinking he was giving Cas a memory he could see for a couple of days, ”Now you can suck my dick.” Dean smirked and switched placed with Cas.

Cas got down on his knees and started sucking on Dean’s balls first. Dean moaned, lightly placing both his hands on the back of Cas’ head, letting Cas work at his own place. Cas finally moved away from Dean’s balls and moved up to his fully erect dick, taking all seven and half inches down his throat. Dean gasped in shock, he thinks the kid might’ve been holding back on his blow job skills the previous night. Unless he was a fast study.

Cas sucked and bobbed his head a lot slower then Dean did to him, it drove Dean nuts. Dean had his eyes closed, enjoyed the sensations of Cas’ hot mouth sucking him greedily. His eyes flew open when he felt Cas’ hand move past Dean’s balls, brushing past his perineum, Cas’ skinny fingers were seeking Dean’s hole, rubbing them cautiously over Dean’s crack.

Dean breath hitched, mainly in shock. Cas looked up at him, silently looking for approval. Dean’s breathing increased, then did something he himself didn’t expect. He shook his head yes.

Cas hummed around Dean’s cock and sprung Dean into action - he widened his stance to make room for Cas’ fingers.

Cas moved his fingers between Dean’s cheeks and started rubbing the outside of Dean’s entrance, circling the area before pressing a wet finger past the ring of muscle. Dean moaned and jerked his hips, Cas moved off of Dean’s dick, taking to just suckling on the head. Cas started to move his finger, pumping the single digit in and out of Dean as he lazily sucked on the tip of Dean’s dick. Dean moaned loudly when Cas curled his finger just right. It had been years since Dean had allowed anyone near his ass, sure he fingered himself quite often but letting someone else do it was just something he never allowed — _but it wasn’t a rule_.

“Ohhh fuck,” Dean moaned. He was close, Cas had only been working for about five minutes, Dean could usually last a lot longer then that. The kid had a natural talent — he’d give him that.

“Faster Cas,” Dean groaned, it felt so good with Cas’ finger in his ass and his pink lips wrapped around his cock. Cas obeyed, simultaneously bobbing and pumping faster.

Dean wasn’t usually too loud in bed but he started to moan loudly with a series of ‘ _Ahhhhs_ ’, ‘ _Mmmm’s_ ’, and ‘ _Ohhhh’s_ ’.

“I’m gonna cum Cas, ohh fuck I’m gonna cum,” and Dean did, his dick erupted come right into Cas’ waiting mouth.

Dean’s first thought was he wanted to do that with Cas again… _and again_ … _and again_ but the thought was quickly replaced by the realization that he needed Cas gone out of his life fast. He couldn’t get attached.

“Was that okay?” Cas asked innocently from where his head rested on Dean’s thigh some come dripping down his chin. Dean had no choice but to laugh at the absurd question.

“ _Was that okay_?” He mocked and pulled Cas onto his feet, “You shouldn’t ask stupid questions Cas.” Dean licked at the left over come then pressed a hard kiss against the teens mouth.

“Get out so I can finished my shower,” Dean said as he shooed him out.

* * *

When Dean reentered the bedroom he was fully dressed in an expensive three piece suit and Cas stood struck, and shirtless.

“Why aren’t you dressed, don’t you need to go?” Dean questioned uninterested while fixing his tie.

“I uh, can’t wear this to school.” Cas held up his mesh shirt from the night before.

Dean chuckled, “Why not?”

“It shows my nipples, my school has a dress code-“ Cas answered before he could stop himself, his eyes grew wide with realization.

“Dress code? At NYU?” Dean quirked an eyebrow.

“I just mean — my own dress code, I have personal standards and wearing a mesh shirt to class is one of them.” Cas lied and laughed nervously.

Dean eyed him suspiciously, “That’s not what you said Cas, you said _your_ _school has a dress code_.” Dean insisted and fiddled with his cuff links. “You don’t go to NYU.” It wasn’t a question. “Cas, how old are you?”

Cas swallowed the lump in his throat, “Seventeen.” He answered softly.

“Son of a bitch,” Dean pinched the bridge of his nose, “You’re in fucking high school.” Dean laughed bitterly, “I should have known. _Idiot_ ,” Dean said to himself and Cas instantly felt bad.

“I-Look I’m sorry Dean but it’s not that big of a deal. I only lied by a couple of years.” Cas apologized with a guilty tremble in his voice.

“You’re underage Cas. You made me commit a crime, ever hear of statutory rape?” Dean scolded.

“Yeah but, the age of consent is sixteen.”

“Not in New York, third-degree rape for anyone age twenty-one or older to have sexual intercourse with someone seventeen or younger. That means up to four years in prison if your parents-“ Dean froze, “Who are your parents Cas?”

“What?” Cas frowned, “Why?” He definitely didn’t want Dean to know who his father was. Not now.

“Because Cas, if they find out and if they’re some homophobic conservatives they could come after me for rape. I’ll be booked in the system as a sexual predator for the rest of my life and even better, I can lose my license!” Dean grew angrier the most he spoke.

“I didn’t think of all that,” Tears threatened Cas’ eyes. His father could ruin Dean’s life if he ever found out. Cas shook his head, “They won’t know I promise, I have a cover story. They don’t care enough about me to question anything and I’d never give them your name. I swear Dean.”

Dean’s shoulders deflated. “Where’s your high school? I’ll give you a ride so you’re not late. I know how schools these days like to call home when a kid is late or doesn’t show up.” Dean disappeared briefly into his bathroom/closet and came back with a black Pink Floyd shirt, “Here, wear this.”

Cas took the shirt from Dean and put it on, it was big on him similar to the shirt he wore the night before. “It’s okay Dean, I can just walk. If I leave now I won’t be late.”

Dean scrunched up his face, “Walk?”

“Yeah googlemaps says it will only take me nine minutes to walk.” Cas answered.

“Nine-?” Dean froze again, “Where do you go to school?” He asked again.

“LaGuardia High School,” Cas knew by Dean’s face he knew of the school.

“The one behind Juilliard?” Dean asked stone faced.

Cas only shook his head, “Yeah I’m going to Juilliard next school year.”

“Your-“ Dean began laughing, “That’s just fucking peachy.”

“Am I missing something Dean?” Cas asked confused by Dean’s reactions.

“Why didn't you find someone to fuck you at school Cas? You go to that liberal ass arts school, I know there has to be loads of little queers around.” Dean jeered.

“I’m not out,” Cas responded quietly, “And my Dad-“ Cas stopped himself, “Just too close to home and I wanted someone with experience.” Cas babbled.

Dean stared at Cas for a long time, “Let’s go.”

“You’re driving me?” Cas asked hopefully. “Googlemaps said to drive it will only take four minutes.” Cas said following Dean down the stairs and towards his elevator.

“Four-FOUR minutes?” Dean banged his forehead against the side of the elevator.

* * *

Dean was panicking - It wasn’t the fact that Cas was underage, honestly Dean had a feeling he was, he was freaking out about how close Cas was to him. Dean spent the entire night before with the comfort that Cas lived all the way downtown near NYU and this morning he finds out his school and his college are only a four minute drive from his house ( _according to googlemaps_ ).

Dean gripped his steering wheel tighter as Cas blabbed about his upcoming symphony finale for school - Dean’s pretty sure he heard Cas say something about the piano. What was meant to be a four minute drive, was turning into a ten minute drive.

“Forgot about the bad morning traffic on West End.” Cas said looked out the impala window.

“Yeah, seems we both forgot that. Thanks googlemaps.” Dean mumbled.

“Thank you for driving me Dean,” Cas turned his head towards Dean and placed his hand innocently on his thigh. Dean heart thumped double time, pausing a moment before removing the offending hand off his leg.

“You’re on the way to my office. It’s fine.” Dean wasn’t doing Cas any favors, if anything this benefited Dean more then Cas. Dean wasn’t sure how it did, but it was the only logical explanation for Dean offering Cas a ride when the dumb kid could’ve just walked.

“Where’s your office at?”

Dean clenched his jaw. “It’s off Broadway.”

“Broadway and what?” Cas pushed again and Dean almost pushed him out of the car.

“66th.”

Cas gasped, sitting up straighter, “No way! That’s literally right across from my college.”

Dean growled, “I know.”

“Wow, small world huh?” Cas nudged Dean with his elbow. Dean glared and Cas only laughed at him.

“Hey, do you know the Nuts For Nuts guy?” Cas asked excitedly.

“I fucking hate the Nuts For Nuts guy,” Dean side eyed Cas, “You know the Nuts For Nuts guy?”

“Oh yeah, I talk to Sal all the time. I stop for nuts sometimes when I walk home from school. I don’t walk too often but when I do I chat with Sal - he has the best stories."

The _Nuts For Nuts_ guy was a man that stood right outside of Dean’s office building trying to selling paper bags of over priced roasted almonds. Cas knew the guy, Cas lived close enough to Dean’s office to walk home. Dean was slowly planning his suicide. 

As Dean rounded 65th street, nearing Cas’ High School - he had to ask. He needed to know, mainly for avoiding purposes.

“Where do you live Cas?” Dean sounded like a scared little girl asking such a stupid simple question.

“Central Park West,” Cas answered simply.

“You live on Central Park West?” In that moment he realized Cas’ parents were loaded to live across from Central Park.

“Yeah, you know John Lennon?”

“Of course I know who John Lennon is Cas.” Dean rolled his eyes, he had a feeling of where this was going.

“Well I live in the building that he got shot in front of. Right across from Strawberry Fields.”

“You live in The Dakota?” Dean’s voice squeaked, “Holy shit.” So Cas’ parents were really _really_ loaded.

“Yeah, it’s okay. There’s always Lennon fans outside taking pictures which is kind of annoying but it’s not bad. You can see the Empire State Building from my bedroom window.”

“Oh whoopee.” Dean remarked sarcastically.

“You’re moody in the mornings, anyone ever tell you that?” Cas chuckled.

“And you talk too much.” Dean smirked back causing Cas to roll his eyes.

* * *

As Dean pulled in front of Cas’ school all the students standing outside turned to look at them. Cas didn’t consider the attention Dean’s muscle car could bring. The teen lit up when he saw his best friend Meg was one of those students, clearly she had been waiting for him.

“So when can I see you again?” Cas turned towards Dean, he made an unreadable expression.

“In your dreams,” He joked with a cocky smile.

“No seriously, let me have your number or something,” Dean frowned and Cas thought maybe he wasn't joking.

“Sorry I don’t have a phone,” He responded as he took out his phone to answer a text.

“Dean.” Cas huffed out an annoyed laugh.

“Go to school Cas.” Dean said not looking up from his phone.

“I-Okay,” Cas deflated sightly, he knew he should've expected it. He knew the kind of man Dean was, but Cas secretly hoped he was different. That Dean actually liked him.

Cas climbed out of the car, “Uh, I guess I’ll see you later?” Cas staged as a question and Dean rolled his eyes.

“Probably not Cas, have fun at school _kid_.” Dean sassed and it only angered him. Cas had Dean dick’s in his mouth not even an hour ago and now he thinks he can call Cas _kid_ , just because he’s a few years younger then what Dean thought.

Cas perked up when he remembered his new job at the Roadhouse and that he would most definitely be seeing Dean again whether Dean wanted to or not.

“I had a lot of fun last night Dean,” Was all Cas said before slamming the passenger door shut and strutting towards Meg.

“That’s the same guy you left the club with,” Meg looked at his shirt, “Oh shit! You actually did it!”

Cas smiled brightly and nodded his head, he looked over his shoulder to find Dean still sitting in his car. “What’s he waiting for?” Cas wondered out loud.

“You have to tell me everything. I want every detail!” Meg grabbed his shoulders excitedly.

“I’ll start by saying, that you were right and the enema was a great idea.” Cas laughed at Meg’s sudden grossed out face.

“Still want all the details?” He smirked.

“Yes. Of course Clarence!” Meg looked over Cas’ shoulder. When Cas looked in the same direction Dean and the impala were gone.

“How was he? Was he nice?” Meg asked.

“I think I’m in love.” Cas said dreamily staring at the place Dean’s car once was.


	7. Chapter 7

**Notes for the Chapter:**

> Thank y'all so much for your lovely comments! I appreciate them.  
> Now on with Dean's not so great day.

“Good morning Mr. Winchester!” Missouri stood from her desk and handed Dean his coffee.

“Thank you,” Dean mumbled barely slowing his stride as he walked towards his office. He sat behind his desk with a sigh, not noticing Missouri had followed him in.

“You have an appointment today with Mrs. Connor about her testament in her husbands murder.” Missouri said quickly, “Also your closing meeting with the Harris family.”

Dean groaned and rubbed his hands over his eyes. Today was not a day he wanted to deal with clients, but with Sam out on paternity leave Dean’s work load was heavier. His chest was feeling heavier, a part of him regretting how he treated Cas that morning as he dropped him off at school. An emotion he wasn't used to dealing with - _regret._ But the kid was sweet and harmless, and Dean needed to learn how to be less of an asshole. He wasn’t sure that was possible anymore. It's just who he was now.

“Mr. Winchester?… Mr-“ Missouri growled, “DEAN!” She snapped her fingers forcing Dean to look at her.

“What?” He shouted back, wanting to retract it instantly. It wasn’t her fault Dean was feeling remorse toward a one night stand for the first time in his life. He couldn’t stop thinking about it… _him_.

“You’ve met him.” Missouri looked over Dean’s face with that look - Dean knew that look.

“No no, don’t start with your weird psychic bullshit. Not today.” Dean denied her but also wondered by what she meant by  _You’ve met him_.

Missouri of course ignored Dean and sat in one of the chairs in front of Dean’s desk. “Remember a few years ago I told you that one day soon you’d meet someone that would make you chance your ways?” She asked.

“No.” Dean remembered, he thought about it a lot actually. She had claimed that one day by fate he would meet his soulmate, that stars would align and Dean would finally be fulfilled. Dean laughed in her face.

“That man with blue eyes.” Missouri mumbled, her eyes still concentrated on him.

“Blue? Blue… eyes?” Dean hadn’t remembered that part. _Cas had blue eyes_ , was his first thought.

“Mmhmm, you were with someone last night, were you not?” She questioned.

“Of course not, Sammy had his baby last night.” Dean lied, he knew it was useless lying to her. He never could.

“I saw the pictures, she is beautiful. Hael, was it? Where did the name come from?” Missouri raised an eyebrow.

“Um, I’m not sure. Jess made it up.” _Stop thinking about Cas_ , _stoping thinking about Cas_. A chant in his mind that actually made him think of Cas more.

“Sweetie, you don’t fool me. You may also want to cover that hickey on your neck boy.” Missouri smirked as Dean’s hand flew to the left side of his neck. Cas marked him. “Unless you don’t want to. You’ve never let a man mark you before, I wonder what was so different about this one. Hm?” She pushed.

“For starters he’s in fucking high school.” Dean snapped bitterly. “Do you have make up to cover this up?”

“Boy are you stupid?”

Dean wasn't sure if she was referring to him fucking a high student or that he asked for her make up that clearly would not match his skin tone.

“I’m guessing that’s rhetorical?” Dean flashed his famous cocky grin.

“High school, huh? I have to admit I didn’t see that coming.” She paused but spoke before Dean could make a snarky comment, “You’ll be seeing him again. Real soon.”

“Yeah okay Missouri, get out and no more of your mumble jumble bullshit.” Dean feared she was right.

After she left Dean collected his thoughts and brought up a map of the upper west side in Manhattan on his computer. His mind raced.

He lived off of 66th, Cas’ building was on 72nd, Cas’ college he’d be attending come fall was between 65th and 66th street, Dean’s office was located directly across the street between 66th and 67th street.

Cas was everywhere and Dean was surrounded. He felt a panic attack coming on.

* * *

“You’re a life savor Benny,” Dean lit up as his best friend walked into his office with two bags of food from the cajun restaurant he owned.

“Thought you might be in over your head today brother, with Sammy bein’ gone,” Benny smiled.

“Let’s go in the conference room,” Dean lead Benny down the hall to the empty room.

Benny paused as he set the bags of food down, and Dean knew he saw it. Benny frowned grabbing Dean’s chin to tilt his head.

“That’s new,” Benny mumbled poking at the hickey on Dean's neck.

Dean moved out of Benny’s grip, scratching the back of his head awkwardly, “Uh yeah-“

“You never let men do that to you,” Benny sat and raised an accusing eyebrow.

“Caught up in the moment I guess Benny.” Dean almost snapped, he didn’t want to talk or think about Cas anymore that day.

“Was it that annoying kid you had with you last night?” Benny jeered.

“He’s not-“ Dean snapped his mouth shut, his first instinct was to defend Cas and now Benny was looking at him like he knew that.

“Forget it Benny, it was an accident.” With a sudden loss of appetite Dean glared at the food in front of him.

“Ya know, you can talk to me-if you need to. About anything.” Benny was sincere.

Dean knew he could talk to Benny openly about anything, they had been friends for over fifteen years, but Benny had a major problem that always prevented Dean from openly speaking with him. Benny was in love with Dean, and Dean knew that - hell, everyone knew that. Dean had tried once, to love Benny, but he couldn’t. Of course he loved Benny but he wasn’t _in love_ with Benny. If Dean really wanted to openly talk to his best friend about how he felt an odd draw to Cas, one he had never felt before, Benny wouldn’t be open about to it - he'd be jealous. Benny would do nothing but hate Cas and Dean didn’t want that, not that Dean had ever planned on seeing Cas again — who was he kidding?

“Uh, the um the guy I had with me last night,” Dean breathed in, “He’s in high school, he lied about his age.”

Benny snickered, “Yeah no shit, any of us could’ve told you that. You really think only with your dick huh? You really couldn’t see he was underage?” Benny shook his head taking a bite of his sandwich.

“I guess I sort of knew, but he was hot and I was horny.” Dean shrugged.

“Story of your life my friend.”

Dean hated when Benny did that. _My friend_ , _buddy_ , _brother_ , all these over used terms of friendship to mask his affections for Dean.

“I guess he’s not going to tell anyone, but I’m worried one day I’ll have a very angry dad knocking down my door with a pitch fork.” Dean snickered.

“Yeah especially his Dad,” Benny mumbled.

“What do you mean?” Dean demanded.

“You didn’t catch his last name, while he wouldn’t stop talking?” Dean had blocked out most of what Cas was saying, especially after Benny was in the car.

“The kids father is James Novak man.”

The blood drained from Dean’s face, “You mean to tell me that Cas-“

“Yep,” Benny made sure to pop the P, “You fucked the son of the Republican senator of New York. Fresh off of Clinton’s reign.” Benny chuckled.

“Call 9-1-1 Benny I’m stroking out,” Dean placed his hand over his upper left arm.

Benny pointed to his arm, “That’s a heart attack brother.”

“Why the fuck didn’t anyone tell me?” Dean groaned.

“Thought you knew.” Benny shrugged.

“You know I don’t learn names.” Dean snapped.

“Funny, pretty sure you said Cas before. You seemed to remember his name.”

Dean ignored Benny, “Senator Novak is a sociopath, everyone hates him! He’s an anti-gay nazi.” Dean said in shock, “I’d feel accomplished getting to fuck his son if I weren’t terrified.”

“Wasn’t he also the governor of New Jersey? During the 90s?” Benny wondered out loud.

“Yes Benny, he was. So glad we had this lunch, I love catching up with you.” Dean said through his teeth.

“It was a pleasure as always Dean.” Benny said too gleefully, “I knew all your fuckin’ around was going to get you into trouble one day.”

Cas lied to him, lied about his age — okay he didn’t lie about his father and he said his last name but Cas should’ve been more upfront. Dean could be in huge trouble and now he was just pissed off.

“I’m so fucked, if I ever see that little asshole again.” Dean fumed.

“Well let’s hope that doesn’t happen,” Benny added, probably for his own person reasons.

“Yes, let’s.”

* * *

“Mr. Winchester, the Harris’ are here in the conference room.” Dean barely raised his head from his desk after Missouri spoke. “Mr. Winchester are you hung over?” She spoke angrily.

“No I’m not.” Dean stood and straightened out his suit.

“There’s a red mark on your forehead from your desk, how long were you sitting like that?” Missouri questioned as she follow him out of his office.

“Since lunch I think.”

“You need to snap out of it, who knew meeting your soulmate took so much out of a person.”

Dean turned sharp on his heel to face her, “Do not say shit like that anymore, I will fire you.” Dean snapped.

Missouri raised her eyebrows, “Boy you are a fool.” She stated as a fact then walked away.

Dean sighed and plastered on a smile before entering the conference room. “The Harris’!” He greeted.

Celeste Harris stood to greet Dean with a hug, “Thank you so much Mr. Winchester, my son is free because of you.”

Dean tried his best not in inhale her strong (probably overly priced) perfume. Dean worked a year on the Caleb Harris case. Caleb was only 25 and accused of killing his own father, Dean had every reason to believe Caleb did kill his father but that wasn’t what Celeste hired him for. A slight weight always pulled at Dean when he knew for a fact that one of his clients did that they were accused of, it might’ve made him a bad person to set murderers free but those murderers paid for his lifestyle. He wasn’t giving that up.

“Yes Dean, I can’t thank you enough,” Caleb shook Dean’s hand with a glint in his eye. A look him and Dean shared often and Dean wondered if Celeste knew her son was gay. Caleb eyed Dean regularly, it was a look Dean knew so well but he had rules. He didn’t fuck clients.

Caleb was handsome with dark skin and light hazel eyes so of course Dean noticed him, and as they sat and debriefed Caleb’s trial Dean kept catching heated glances from the man. Dean was on a streak with breaking rules so maybe — just maybe.

“I think we’re all done here, please excuse me I need to use the restroom,” Dean cleared his throat, throwing a glance towards Caleb’s direction hoping he’d get the hint.

 _Bad idea_. What was Dean thinking? Inviting a now former client (and murderer) to the bathroom for a hook up. Dean knew he was trying to prove something, prove to himself that all his rule breaking wasn’t just because of Cas - there was just something off about him, it wasn’t just Cas. It wasn’t.

When he heard the bathroom door open, Dean flicked his hands dry after washing them looking into the mirror and at Caleb who now stood behind him at the door. Caleb raised an eyebrow and locked the door. It was go time.

“You know why I killed my father Mr. Winchester?” Caleb asked slowly.

Dean snickered, “Not something you should say to your lawyer that just got you off for murder.”

Caleb rolled his eyes, “Don’t act like you didn’t know.” Of course Dean knew.

“My father was an asshole, a homophobic, abusive asshole. The world is better without him. My mom is better off without him.”

Dean turned around leaning back against the bathroom sink, his hands gripping the edge with his hips left on display — another invitation.

Caleb smirked and licked his lips moving towards Dean.

“We’ve all had our daddy issues,” Dean whispered as Caleb stepped into his personal space.

“Hm, wonder what daddy would think about me sucking my lawyers dick in the bathroom of his office.” Caleb reached for Dean’s belt, pulling it off cooly.

“Guess we’ll never know.” That sinking pit in Dean’s stomach screamed again.

The feeling was lost as soon as Caleb sunk to his knees pulling Dean’s pants and boxers down to pool at his ankles. Dean groaned as his wet mouth engulfed him. Caleb was good at sucking dick, but lacked the passion Cas had. Dean wondered when passion started to matter.

Dean took too long to cum, Caleb’s lack of enthusiasm threw off what could have been an amazing blow job. Caleb however looked over satisfied with himself, as Dean tucked himself back into his pants he knew he had to returned the favor. He didn’t want to but he didn’t want to be rude.

Caleb didn’t take long to cum and hat placed a slight pep back in Dean’s step, he had been off since last night but he knew how to please a man and he was good at it.

* * *

“You’re in a significantly better mood,” Missouri raised an eyebrow, “What did you do?”

Dean gasped in fake horror, “What makes you think I did anything?”

“Mrs. Connor will be here soon.” She reminded him.

Dean groaned hitting his head against the front desk she usually sat at, “Defenitally not in the mood to deal with Mrs. Connor.”

“Mr. Winchester-“

“I fucking hate dealing with widows,”

“Dean-“

“They’re all cunts,”

“Mr. Winchester!” This time his name came from behind him and not from Missouri.

“She’s behind me, isn't she?” Dean whispered towards Missouri.

“I tried warning you,” She shrugged her shoulder.

As soon as Dean turned there was a small cold hand striking him across the face.

“You’re fired!” Mrs. Connor yelled.

“And you’re still a cunt!” Dean shouted back, various people in his office all stopping to watch.

“I’m getting a new lawyer, and you’ll be hearing from them,” She huffed.

“Yeah sure if you get off for killing your husband you gold digging bitch,” An audible gasp was heard around the lobby of Winchester & Winchester Law.

Mrs. Connor stormed out, taking the stairs instead of the elevator. Dean gave her props for choosing a more dramatic exit as she slammed the door to the stairwell.

“I think you should go home Dean,” Missouri said very seriously behind him.

“I’m not going home,” Dean turned to face her, “I’m going out.”

Dean chose his less dramatic exit, pushing the button for the elevator and waiting while a burst of murmurs erupted behind him.

Dean didn’t go out, Dean ended up driving straight home and without noticing he drove a different route passing Cas’ school along the way.

“Get over it,” Dean cursed himself. Get over what? Cas? His mistakes? The voice growing louder telling him he isn’t really as happy as he tried telling himself he is?

Dean got drunk and passed out, purposely ignoring the several text and calls from his brother. At least the voice shut up.

**Notes for the Chapter:**

> I'll be uploading the next chapter next week instead of two weeks because the next chapter is just Castiel's version of "the day after". Then the boys will be reunited. Oh joy!


	8. Chapter 8

**Notes for the Chapter:**

> Like I said a chapter a week early. Here's Castiel's day after.

“Nice shirt ASStiel!” Cas grunted as he was shoved from behind.

“Fuck off Luke!” Meg spat grabbing at Castiel’s elbow helping him stand straight.

“Where did you get it?” Luke asked ignoring Meg. “From your boyfriend you little fag whore? Everyone saw you this morning being dropped off in that car. Is he your pimp?” From behind look his two goons Naomi and Raphael snickered.

“Why don’t you crawl back into your mothers vagina _Lucifer_ , and take the ninja turtle with you.” Luke snickered at the nickname as Raphael glared at Castiel.

“You’re such a little loser Castiel, I can’t even be insulted by you because you’re so pathetic.” Luke turned away snapping his fingers for his friends to follow.

“Later losers,” Naomi flicked the middle of Meg’s forehead before walking away, Cas had to stop her from attacking.

“I can’t believe you’re related to that bitch.” Meg glared at the back of Naomi’s head now down the hallway — the three were terrorizing some freshman.

“She’s just my second cousin, and you’ve met most of my family is that really hard to believe?” Cas snickered, it was safe for Castiel to say that he was the black sheep in his family. Even his wayward brother Gabriel fit in better. For a time Castiel truly thought it might be because he didn’t belong anywhere, but he knew there was a life outside of his families bubble that was waiting for him to come home to. He just needed to find it, he wondered if that life was with Dean.

“God, could they be anymore stereotypical bullies?” Meg said as she watched Luke giving the freshman a noogie. “Luke is so awful.”

“He wasn’t always like that,” Cas said sadly.

“Oh yeah…” Meg frowned at her friend.

It was no secret between the best friends that Luke had been Cas’ first kiss. The two of them where once very close, when they were twelve Cas developed a crush on Luke. When they were thirteen Luke appeared to return his feelings, at the time it was all innocent kissing and hand holding for the two but it only lasted about a month.

When the pair reached high school Cas moved to New York leaving Luke behind in New Jersey. They had lost touch but when sophomore year started Luke was back at Cas’ school only he was different — meaner, angrier and he hated Cas for no reason.

“I should get to class,” Meg said bringing Cas back to the future. “But before I forget,” Meg reached into her backpack pulling out one of Castiel’s button up shirts.

“You’re a life saver Meg, could you imagine if I went home in this?” Cas gestured to Dean’s shirt he was wearing.

“That’s why I brought it. I waited outside for you because I thought for sure you were going to stroll up in that gay ass mesh shirt.” Meg chuckled.

“Leave my gay ass alone,” Cas shot back playfully.

“Bet you weren’t saying that last night,” A suggestive smirk played on her face.

“No I was not.” Cas chuckled. He was elated he would be seeing Dean again soon, but there was worry nudging the back of his mind that Dean might really not want to see him again. He tried to shake the feeling off as he headed off to class.

* * *

“Hello Mr. Novak.” Frank greeted Castiel as he yanked opened the back seat of his family’s black 2016 Lincoln.

“Hello Frank,” Cas mumbled. Cas hadn’t had a terrible day at school, no more then usual, but something was off. Castiel was used to Luke and his goons giving him a hard time at school it usually didn’t effect him but he had been in a bad mood since their confrontation that morning.

“Your father and mother are in Washington D.C, last minute trip-“

“So that means Linda’s there?” Cas groaned.

“Sorry, sir,” Frank’s eye’s flickered up towards the rear view mirror to look at him.

“I’m seventeen, I don’t need a nanny anymore.” Cas folded his arms to pout.

“Of course not.” Frank chuckled.

Frank Devereaux had worked for Novak’s since 2008 when James was first elected New York senator. He personally worked for Castiel as his driver and personal security guard. The concept that Frank was meant to protect Castiel always made the teen laugh — the man was paranoid possibly boarding on insane. But Cas liked Frank so he never told his father how many times Frank tried to attack a squirrels in Central Park because he thought the squirrel was a threat.

“Frank, may I ask you a question?” Cas asked.

“Of course.”

“Tomorrow-“

“Is Saturday,” Frank offered unhelpfully.

“Yes Frank I know, but I have somewhere to be… in the afternoon.” Cas hadn’t really thought about what he was going to tell Frank about his new job at the Roadhouse. He needed rides but couldn’t really tell Frank he was working, he liked Frank but at the end of the day he worked Castiel’s father - Castiel couldn’t have Frank snitching about his new job. Maybe it was high time Cas learned how to navigate New York’s subway lines.

“Where, sir? I’d be happy to take you and Mrs. Tran.”

“No. I need to go by myself, Linda cannot come.” The situation was going to be harder then he thought.

“She has to go with you, your father said.”

Cas sighed, “Never mind Frank.” Cas was going to have to figure something else out. There was no way he was going to miss out working at the Roadhouse, he needed it.

* * *

“Castiel, please, your mother gave instructions. How long have we been doing this?bYou know the deal.” Linda Tran spoke desperately.

“It’s just a couple of hours Mrs. Tran, I’m seventeen years old!” Castiel argued.

“And a seventeen year old boy does not need to be running around Manhattan unsupervised.”

Castiel wondered what his parents and Mrs. Tran would think about what he was doing the pervious night. He smirked at the thought of his father’s head literally exploding.

“I’m not running around, I’m meeting a friend.” He wondered how many times he could get away with the Meg lie.

“Yeah a female, do your parents know this girl?”

Castiel growled, “That’s it, I’m calling mother!” Castiel couldn’t think of a time he sounded snootier — desperate times called for desperate measures.

Castiel stomped his feet towards his parent’s land line, dramatically punching in his mother’s phone number in true brat fashion.

“Linda? Is something wrong?” Amelia answered.

“It’s me Mama.” Castiel shot a quick glare at Mrs. Tran.

“ _Zdravstvuj_ Castiel, I’m busy — what is it?” Amelia sighed impatiently.

“Mrs. Tran is ruining my life,” Castiel was never one to miss an opportunity to be dramatic.

“Oh Castiel, really?” Cas could hear the eye roll, she had heard this from her son many times.

“Yes really, I’m meant to meet Meg tomorrow — to go over our sheet music for our final recital, it’s very important to my grade all my hard work would’ve been for nothing and Mrs. Tran isn’t letting me go and she’s hovering Mother!” Castiel spoke fast with the intention to annoy his mother, he knew how to get to her.

“Castiel, stop! Meet Megan tomorrow and-“

“Tell Mrs. Tran,” Castiel stopped his mother and held the phone out to his nanny.

With a smug smirk Castiel watched as Mrs. Tran submitted to his mother instructions. He won. It was a rare that Castiel didn’t get what he wanted.

“You can meet your friend tomorrow, Frank will drop you off.” Linda said stiffly.

“That’s all I wanted Mrs. Tran,” Castiel smiled sweetly at her.

“I don’t know why I argue with you,” she shook her head, “Not sure why your parents still keep me around, I leave my own sixteen year old alone to be here with you.”

“Tell me about it.” Castiel rolled his eyes moving past her to lock himself into his bedroom.

As Castiel laid out on his bed, staring at the glow in the dark stars he stuck on his ceiling when he was fourteen, he couldn't help but wish Dean had given him his number.

Castiel successfully moved on with his day, but now that he was _still_ \- he ached for more. The teen had a taste of a life more interesting and he wanted to live in that world. He needed the job at the dinner, he needed to be surrounded by Dean’s people. They were real, everyone in Castiel’s life was fake.

Most importantly he needed to see Dean again. He wondered if he would see Dean tomorrow — about a million different scenarios about seeing Dean again ran through his head. Dean’s green eyes lighting up with excitement as he tells Castiel he was special and was glad to be seeing him again, ending with Dean giving him his number and an innocent kiss on his cheek — that was Castiel’s favorite scenario. He didn’t want to think about the bad reactions Dean could have, or Dean not showing up at all.

**Notes for the Chapter:**

> Castiel's mom said Hello in Russian.
> 
> That's that for Castiel's and Dean's individual chapters, two weeks and we will be back to usual programming, our boys will meet again!


	9. Chapter 9

“This diner sir?” Frank eye’d the Roadhouse diner suspiciously, “Not really the usual place you go.”

“And what usual places do I go Frank? I’m almost always at home or at school.” Castiel pointed out.

“Alright then, I’ll wait here.” Frank parked the car along the sidewalk and started to pull out a book.

“No!” Castiel shouted then cleared his throat, “I mean, I may be awhile. Just go home and I’ll call you.” Castiel instructed calmly.

“I really can’t do that.” Frank raised his eyebrows.

“Please don’t make me call my Mother,” Castiel threatened lightly.

“Fine, call me when you’re ready,” Frank sighed, “But I’m watching you walk in.”

“Sure Frank,” Castiel chuckled and exited the back seat of the car.

Castiel let out a nervous breath before walking across the busy street towards the Roadhouse diner. When he and Ellen briefly talked about the diner she certainly wasn’t wrong when she said it wasn’t much.

The Roadhouse diner sat on the corners of West 75th street and Amsterdam. The outside of the diner was painted a nice royal blue, Castiel thought it looked like it had been redone recently. On top of the diner sat a four story red bricked apartment building and the teen wondered if that’s where Ellen and Mary lived.

Mary had told Castiel that after she became sick again she gave up her own apartment and moved in with Ellen and her boyfriend Bobby who owned his own car garage.

Before Castiel reached the corner side walk, a royal blue door (that had seen better days) swung open. Castiel’s nervousness suddenly disappeared when he saw Mary waving him over to the door.

“10:00am, right on time,” She smiled wiggling a beaconing finger and moving to the side letting Castiel step into what he now saw was the kitchen of the diner. “That’s quite the fancy car you were in,” Although Mary tried her best to sound upbeat Cas could hear the weakness in her voice, he momentarily frowned. He wasn’t sure how bad her cancer was — he was starting to figure out it wasn’t very good.

“Rich kid.” Castiel shrugged.

“Indeed,” Mary scanned his body, Castiel shifted under the scrutiny. “Dress shoes and slacks?” She quirked an eyebrow that reminded him so much of Dean.

“I uh - wasn’t sure what to wear.” Castiel answered sheepishly, taking a quick look around the kitchen. There appeared to only be one cook - Cas took note of the mullet.

Mary giggled, “We have Roadhouse shirts for you to wear, just a plain white golf tee with our logo but I suggest you start wearing jeans and white tennis shoes. You’ll be on your feet the whole day,” She pointed at his black dress shoes, “Those won’t do.”

Cas nodded in understanding following Mary who silently told him to follow into a back room connected to the kitchen. The room was a small office with a simple desk, chair, some filing cabinets and brown boxes scattered. Cas felt the urge to organize immediately.

Mary opened one of the boxed and pulled out a couple of white collared shirts. “Here,” she handed one to Castiel. Castiel stood for a moment with the shirt in his hand not really sure what to do.

“Go on and change into it dear, you have nothing I haven’t seen before.” Mary smirked and turned around to open one of the filing cabinets. Feeling suddenly shy the teen quickly unbuttoned his white button down and pulled the shirt over his head.

“Hm, a little big but I’m sure it will shrink in the washer,” Mary looked over her shoulder at him.

“Maybe I’ll grow into it,” Castiel joked.

“Oh hopefully you won’t be here that long,” Mary now held some papers in her hand and squinted at him, “Shouldn’t you be done growing?”

“I’m seventeen,” Castiel bit his lip, “Is that okay?”

“I didn’t believe you were nineteen sweetie,” Mary smiled and handed him the papers, “Here, I need you to fill these out for me before we get started today.”

Mary took a seat behind the desk and Castiel followed her lead by taking the chair the that sat in front of the desk. He watched her carefully as she fiddled with the white scarf wrapped around her head.

Mary caught Castiel’s eye and smiled, “I have no hair,” He looked surprised, “If you were wondering.” She finished.

“O-oh I wasn’t.” He was.

“It’s okay, maybe one day I’ll show you,” Mary looked down, her facial expression shifting to something sadder, “I don’t look great bald, I’ve got one of those weird bumps in the back — some women can pull it off but not me.” She chuckled but didn’t smile.

“What about wigs?” Cas inquired.

“Itchy, I hate them,” She smiled this time. “Go on and fill out those forms honey.” She encouraged.

* * *

Dean groaned loudly as his phone rang for the fifth time that morning.

“Shut up!” He yelled and threw the bottle of empty whiskey must have fallen asleep with toward the noise. Dean was hungover for the first time in a long time, usually he knew how to pace himself, how much to drink and when to eat to avoid the headache the next morning. He couldn't remember the time he was so careless with his drinking, and as Dean laid completely naked on his couch - he was suddenly reminded of his father.

“ _You’re going to turn into your father if you don’t quit_ ,” Dean mocked his mothers voice from the past, “Quiet Mom.” He whispered to someone who wasn’t there.

Dean must’ve fallen back asleep because the next thing he knew he was being woken by someone shaking him.

“What the fuck?” He croaked out and squinted at his intruder. “Benny?”

“You look pathetic brother,” Benny shook his head.

“What time is it and why are you in my apartment?” Dean tempted to sit up only to flop back down, completely uncaring that he was flashing Benny.

“It’s about 11:00 in the morning and your brother has been calling you, he was worried so he called me to check on you.” Benny grabbed one of Dean’s throw blankets and threw it over his lap.

“Don’t you have anything better to do then check up on me all the time?” Dean questioned in spite because of his own embarrassment.

“It’s my job Dean, I’ve been doing it for years and I’ll be doing it till we’re old and gray.” Benny was no longer standing in front of him, his voice was carried from the kitchen down.

“Maybe you should get a life then Benny, because that’s pretty sad,” Dean didn’t mean to say it - but maybe he did.

He heard Benny laugh, “That’s nothing I haven’t heard before.” Benny replied returning with a glass of water and aspirin.

“Thanks,” Dean mumbled as he sat up taking the pills and water. “I’m glad you don’t have a life Benny, you’re too good to me.” Dean gave Benny a sheepish smile.

Benny hummed in response handing Dean his phone, “Call Sam.” Benny stood and pressed a quick kiss to the top of Dean’s head, “And take a shower.” He ordered before moving towards the elevator.

“Wait, where are you going?” Dean frowned.

“Roadhouse, or are you forgetting our weekly Saturday lunch meetings,” Benny smirked.

“Can’t you wait for me so we can go together?” Dean asked, unsure if he was going to go at all.

“No can do brother, I have to beat Charlie before she queues up the jukebox with nothing but the song _Benny and The Jets_.” Benny grumbled.

“Again.” Dean smirked, Charlie knew Benny hated that song so forcing him to listen to it over and over while they ate was her favorite pass time.

“I gotta go,” Benny moved quickly toward the elevator.

“Thank you!” Dean shouted after him, “You’re my best friend.”

“And you’re a pain in my ass,” Benny shouted back.

“You wish.” Dean chuckled.

* * *

Mary left the diner after introducing Castiel to everyone ( _Ash the cook_ ), Castiel already knew Jo and Ellen, Mary told him he would be shadowing Jo for the day and cleaning the tables off.

The work didn’t seem too hard, Jo quickly found out Castiel had an excellent memory, she’d jot down a tables orders and before she could shout it back to Ash Castiel was telling the cook the order word from word without reading it off of Jo's notes.

“Are you some sort of genius?” Jo asked with an impressed expression.

“I’m a pianist, I’m an excellent listener and observer.” Castiel explained.

After Jo learned Castiel was a pianist she suggested the nickname _Mozart_ to her mother. Ellen just squinted her eyes at Castiel and shook her head, “It’s not right — the name will come to me.” She said almost ominously. Castiel hadn’t realized how serious Ellen took the nicknames at the Roadhouse, he slipped up a couple of times by calling Jo by her name instead of _Watson_ \- he received deadly glares from Ellen every time he did it while Jo simply ignored him until he got the name right.

By noon the morning rush had died down and Castiel was grateful for it. Being overly in tune with noises was both a blessing and a curse. Castiel could easily zone in on a symphony and pick apart the music — but when it came to loud, crowed spaces he often got overwhelmed giving him instant headaches. Castiel feared he would have to inform Ellen that he couldn’t work at the diner during the busier hours, the clanking of places, people chattering in many different conversations along with the noise of the juke box was all a but much for him.

“Castiel are you alright?” He jumped when Jo appeared behind him, he was standing in the kitchen loading the giant dishwasher.

“Oh yes, I zoned out for a moment. Sorry.” Cas apologized, Jo just waved it off.

“I want you to wait on a table,” She smiled, “ _by yourself_ , I think you can handle this one.” She winked at him.

“Uh, okay,” Castiel nodded, he could handle that, he could take orders but his worry laid in the social aspect. Castiel had a hard time talking to people and connecting, both Jo and Ellen were loud and personable he didn’t know how to be that. Castiel just rambled to anyone he thinks could be listening, often about the wrong things.

Castiel wiped his hands on his white apron before taking it off and handing it to Jo. She gave and encouraging smile and thumbs up - that moment Castiel realized he really liked Jo, she was kind of the older sister he always wanted. He never got along with Anna like he hoped to get along with Jo.

Castiel’s heart pounded when Jo pointed towards the table he’d be waiting on. He recognized Benny, and Charlie but there two other men there he didn’t recognize - _No Dean_ , he observed disappointedly.

“Um Hello,” Castiel greeted the table - The shocked and disgusted look on Benny’s face worried him.

“Castiel!” Charlie smiled happily at him helping him to relax. “How’s your first day going?”

“It’s going,” He smirked and swallowed the lump in his throat trying to avoid Benny’s frown.

“What’s he doin’ here?” He asked Charlie.

“Uh well, Jo told me Ellen hired him at the hospital,” She explained slowly, “The take over for Mary,” She added sadly.

Charlie’s comment only seemed to anger Benny, “Does Dean know that?” He spat out.

“Relax Cujo,” Charlie said back, “I’m sure Mary would’ve told him.”

“You better hope so or there’s going to be scene here in about ten minutes.” Benny folded his arms over his chest and Castiel felt his heart pummel. Did Dean say something to Benny? Was Dean mad at Cas for lying about his age?

_Dean was coming._

“Is there a problem?” Castiel asked Benny bluntly.

Benny wouldn’t look at Cas, “Yeah you,” He mumbled.

“Chill!” Charlie glared at him. The other two men that Castiel didn’t know exchanged confused looks.

Benny leaned over a bit closer to the two men across from his, “This,” Benny jerked his head towards Cas, “Is one of Dean’s one night stands and now he’s working at his families diner.” A tone of bitterness underlined the sentence.

“Yikes.”

“Oh shit.”

The two men said together.

“Am I missing something?” Cas asked desperately.

“Guess you’ll find out when Dean-o gets here.” The rougher looking one of the two men snickered.

“Long story short kid, I saw Dean jump out of a two-story window to avoid seeing someone he fucked again,” The other one said.  
  
Castiel felt his body tense up, “I-“ He stopped himself from asking any further questions, Charlie looked at him with sad doe-y eyes. “Can I take your order?” He cleared his throat.

The four exchanged odd looks before ordering.

_A Grand Slam Breakfast Plate_   
_The Roadhouse Sandwich Box with no onions_   
_An Avocado Turkey Grilled Sandwich with Fries_   
_Chicken Fingers with Onion Rings_

“Got it.” Cas nodded his head but as he walked away one of Dean’s friends stopped him.

“You didn’t write it down,” He quirked an eyebrow.

“It’s up here,” Castiel pointed to his head.

The man snickered, “I’m Aaron by the way,” Aaron pointed to the man next to him, “and this idiot is Cole.”

Castiel looked between the two men, confused by their smiling faces, “It’s nice to meet you.” Castiel frowned trying to figure out if they were making fun of him or not, he never had a good read on people. Unless they were deliberately mean to Castiel's face, he often missed when people were making fun of him. Meg always said it was because he had Aspergers, Castiel assured her he didn't - it was because his social conditioning growing up had been poor. That wasn't his fault, as he grew older he realized how much he needed curtain social interactions. Now people just thought he was weird or annoying. He needed the job at the Roadhouse, he needed to learn and he wanted Dean to teach him.

* * *

Dean felt better after his video chat with Sam. It cheered him up to know that his niece and Jess were doing well. Sam had insisted that Dean visited but he wanted to leave the new family alone for a while.

As he got ready to meet everyone at the diner Dean had a sick nervous feeling and he wasn't sure why. On the way he had gotten an ominous text from Aaron with a bunch of laughing emojis. He knew it couldn’t be good, Dean wondered if his mom was telling embarrassing stories about him again.

Dean quickly spotted his friends in their usual corner booth, being at late as he was everyone had their food.

“Sup, losers,” He greeted forcing Benny and Charlie to scoot so he could sit.

“Oh, not much,” Cole had one of his shit eating grins on his face.

“Oh really?” Dean raised an eyebrow in suspicion.

“Dean we need to tell you-“ Charlie was quickly hushed by all three men.

“What me what?” Dean demanded.

“Don’t say anything Red!” Aaron pointed threateningly at her, “This is going to be SO good.”

“It’s not about him it’s about-“ Benny shushed her and pointed toward the kitchen.

Dean frowned and followed where his finger was point.

“Oh no,” Dean felt like all his bodily organs just dropped out of his ass and onto the floor.

Dean felt his ears burn and his heart thump hard against his chest - fuck was he actually sweating? He heard Aaron laugh about Dean blushing - Dean wasn’t blushing, Dean was fucking furious.

“Um hi,” Cas smiled shyly.

“What the fuck are you doing here?” Dean snapped, “What the fuck Cas?”

“Dean!” Charlie scolded while Cole, Benny and Aaron all hid smiles behind their hands. Cas turned red and looked at everyone but Dean.

“I-I work here, Ellen and your mom-“

“Where’s my mom?” Dean looked behind Cas toward the kitchen. That’s when everyone froze, Dean could feel the sudden drop - the sudden realization.

“Mary hired me in her place, she- she went home.” Castiel explained.

“She went home?” Dean grew more furious, “When the fuck did she hire you?”

“The other night, at the hospital, she said she wasn’t really able to work any more so-“

“I gotta go,” Dean interrupted stand up and pushing Cas aside to storm out the door.

“Dean!” He heard Benny call.

“Fuck off Benny,” He mumbled and made his way through the diner, he didn’t care people were staring he was pissed.

“Dean please wait-“ He felt a hand grab his elbow. Dean turned sharply, almost causing Cas to fly into him.

“I should’ve told you I was working here and-“

“I don’t give a fuck Cas, _really_. I do not care even a little ounce about what you do or care about you period — you’re a tiny blimp in my life. You don’t exist to me.” Dean spat, “If I think you’d listen to me I’d tell you to quit and fuck off somewhere else Cas because I don’t care to see you.” Cas eye’s widened and took a step back, but Dean wasn’t finished. “You should’ve told me who your father is, does Ellen know your James Novak’s kid? A snobby little rich cunt - working here? Taking a job from someone who actually needs it.”

“I _do_ need it.” Cas said quietly.

“Of course you think so, you over privileged asshole. You’ve never had to work a day in your life and now you suddenly think you need a minimum waged job? I know what you’re doing Cas and it won't work. Leave me alone.” Dean took one last look at Cas’ shell shocked face before storming out the front door.He didn't feel bad, he felt numb - why had his mom stopped working. And why, of all people, did she hire Cas? The stupid teen had been on Dean's mind ever since he dropped him off at school the previous morning. Seeing him in a place he considers a home, struck a nerve. 

* * *

When Cas turned around, everyone was looking at him. Dean caused a scene and to say Castiel was embarrassed would be an understatement. Castiel walked numbly toward the kitchen when he was met by both Ellen and Jo.

“Look if you want to fire me, it’s okay.” Castiel shook his head in defeat.

“Oh sweetie I’m not firing you - hell you’re probably the best waiter we’ve had in a while. Loads of potential.” Ellen gave him an encouraging smile.

“Dean’s an asshole Cas, I’m so sorry he just did that to you — he’s always been-“ Jo shook her head, seemingly lost for words to describe Dean.

“That wasn’t about me,” Cas said quietly, “No one told him his mom was too sick to continue working - including his mom. He’s hurt.”

Both Ellen and Jo smiled, “You’re a smart kid.” Ellen pulled him into a hug which he didn’t feel like returning, he let his limps hang loosely to the side.

“So you’ll still work here?” Jo asked hopefully.

“Yes, I like you guys and Dean -“ Cas looked down, “Dean will get over it.”

A trait that Castiel possessed and always felt proud of was that he was determined, he never cared who or what tried to bring him down — he did what he was going to do and he wasn’t going to let nay sayers stop him.

Though Castiel was determined, in that moment Castiel wished he was a little bit stronger, Dean may not have meant all that he said (or maybe he did) but his words hurt Castiel. The teen could hold his head high for the rest of the day but he knew he needed to go home and have an excellent crying session over Dean later.

Cas sighed and did what he dreaded to do — return to Dean’s friends’ table. He didn’t want to see the smug faces of his friends, all they wanted was a show and that's what they got. Like Castiel was there for their entertainment.

But when Castiel reached the table he was met with the opposite.

“Cas, are you okay?” Charlie furrowed her eyebrows.

“Yes Charlie I’m fine,” Castiel answered stiffly.

“Man that was - I really didn’t expect him to unload like that,” Cole shook his head in disappointment.

Castiel tilted his head taking in their sympathetic expressions. “Please, I don’t want your pity.”

“We just want to apologize for Dean.” Charlie explained quickly.

“Only Dean can apologize for Dean.” 

**Notes for the Chapter:**

> I just realized this is a week late - sorry xx.  
> I don't want to leave you hanging with Cas and Dean on bad terms so the next chapter will be up by next week.


	10. Chapter 10

**Notes for the Chapter:**

> I feel like there should be a warning in this chapter, a character is suffering through terminal cancer, just in case that may be triggering to you.

Dean rounded the corner heading straight towards the green awning that lead to the apartments above the Roadhouse. Being in a rush, and completely seeing red, Dean took two steps at a time towards the third floor. He didn’t seem to have the patience for the buildings crappy elevator.

He didn’t bother knocking when he reached his mothers and Ellen's shared apartment, he went straight for his spare key that he owned.

“Mom?” He shouted out as he entered the front hall. “Mom?” He said louder when he didn’t receive an answer.

“What Dean?” Mary’s groggy voice came from the sofa.

“Were you sleeping?” Dean’s heart dropped when he saw her appearance, it was rare when Mary didn’t have a scarf on covering her bald head. Dean had only seen her without one once when she first started treatment - it was hard not to stare. When Dean was younger he loved playing his mom’s long beautiful blonde hair, seeing her with no hair, seeing her sick, Dean never coped will with it all. Not like Sam.

“Yes Dean, I was,” Mary frowned and struggled to sit herself up. She immediately went to reach for her head scarf sitting on the coffee table but Dean stopped her.

“Dont. You don’t have to wear it.” He carefully took a seat next to her, momentarily forgetting the reason he was there and that he was pissed.

“I know it upsets you,” The right corner of her mouth lifted in a half smile - her lips pale and chapped.

“It’s okay,” Dean placed a hand gently on her back, she gave him a grateful smile and suddenly, he remember why he was there.

“Why didn’t you tell me?” He wanted to sound angry, he wanted to shout at her - he ended up sounding more hurt then he wanted to.

Mary sighed, and Dean knew he didn’t need to explain what he was talking about.

“It’s time for me to stop Dean, I’m sorry I didn’t tell you - I didn’t know how.” She looked away from him almost ashamed.

“No,” Dean shook his head, “It’s not time - not yet. The diner isn’t the same without both you and Ellen there. It-It doesn’t feel like home.” Dean dropped his hand from her back to fold his arms across his chest. Closing himself off, like he always did.

“Oh Dean,” She looked at him with a sad pout, “I know this has been hard but-“

“I know.” He interrupted quietly, “I get selfish about these things, it’s hardest on you.”

“That’s not completely true Dean, I’m the one dying - You and Sam? You’re left with the pieces and I’m so sorry.” Tears welled in her eyes.

“Mom no-“ Dean chocked, holding back a sob. “There’s still time and still hope, you still have your treatments.”

“I guess now would be a good time to tell you Dean,” She arranged herself to face him, “They’ve stopped my treatments about a week ago.”

Dean heart thumped hard in his chest, it was the last thing he ever wanted to hear. “What- what else are they going to try?”

“Nothing,” Mary shook her head, “That last treatment was my third go, my last go, Dean.”

“So they’re just not doing anything anymore? Nothing?” Dean asked desperately.

“There’s nothing left honey, I’m so sorry.” Mary hung her head. Dean didn’t - _couldn’t_ \- say anything. He held Mary to his chest for a while until they naturally broke apart. He wanted to ask her how long she had or how she long she _felt_ she had but he couldn’t get those words out. He didn’t want to know the answer.

“I have to apologize to Cas.” Dean mumbled and looked down as Mary pulled away from his embrace.

“What did you do to him?” She sighed, Mary knew Dean all too well.

“I said some stuff I shouldn’t have,” Dean shook his head, “But you should have told me you were quitting and was hiring him.”

“I know, I should have told you.” Mary patted Dean’s knee lightly.

“Cas doesn’t need that job, can’t you hire someone else?” Dean asked grumpily.

“He needs a family,” Mary smiled, “He’s a little angel.”

“Jesus,” Dean rolled his eyes and thought about telling his mother he didn’t moan or give head like an angel. “You know who is father is right?”

Mary chuckled, “I do. I also know he’s only in high school.” She smiled.

“Why are you smiling?”

“I’m just picturing what your face might’ve looked like when you found out both those things.” She giggled.

“Very funny,” Dean smirked, “I actually drove him to school yesterday morning. I had to drop a guy I picked up at a night club to High School the next day,” Dean shook his head as Mary let out a boisterous laugh.

“Oh honey, I needed that laugh, thank you,” She said through a fit of giggles.

“Glad my misfortunes can make you happy.” Dean glared playfully.

“Go say sorry to Castiel, for whatever you said. He’s sticking around, get used it.”

Dean nodded solemnly. He didn’t need to be friends with Cas, he just needed to make nice for the sake of his mother.

* * *

Cas was never one to be changeable. His entire life consisted of consistency and familiarity. The rollercoaster of emotions he had experience in the last few days had thrown him for a loop, he was changing, he was learning and he was growing - Finally feeling some freedom from his small cage.

So it didn’t surprise Castiel too much that only an hour ago he had experience a slight heartbreak and public humiliation to now, laughing and drinking coffee (he was never allowed coffee) with Dean’s friends. Despite Dean's outburst and obvious resentment, he still felt happy.

He found Aaron and Charlie to be the smart sensible ones in the group, Cole was a bit of a meathead and Benny didn’t give much to Castiel for him to get a read on — one thing Castiel knew  was that Benny was protective of Dean, in a way Castiel hadn’t really seen before. Perhaps brotherly? He wouldn't know he wasn’t close to any of his brothers. Maybe he loved Dean? Castiel wouldn’t know that was either - he had never been in love. But he would certainly like to try.

They were currently exchanging embarrassing school stories, and Cole had been in tears over Castiel’s. “You really just walked up to him and said ‘Mommy can I use the restroom’?”

“It really isn’t that funny,” Castiel smirked, the coffee was making his heart jump and hands shaky. He hoped it wasn’t noticeable.

“It is pretty embarrassing Cas,” Charlie giggled, “I mean it’s one thing to call a teacher Mommy, but to call a _male_ teacher Mommy is just too funny.”

“I was only ten,” Castiel defended again. “At least I didn’t wear diapers until I was five,” He shot a hard glare at Cole.

“You got me there buddy,” Cole raised his hands in defense. “You know,” Cole said thoughtfully to Cas, “You’re all right kid.” Cole nodded with approvement.

“Uh thanks,” Cas mumbled in shyness, one thing he was used to — acceptance.

“Cas?” The group jumped at Dean’s sudden presence at the table.

“Can I talk to you?” Dean asked when Castiel didn’t reply. “Outside,” Dean took a quick glance at his friends, he looked… embarrassed.

“Whatever you need to say to Cas, you can say here.” Charlie said protectively. Castiel didn’t need protecting, especially from Dean, but he still appreciated her response.

“What are you now, his watch dog?” Dean glared at his friend, “Let Cas decide what he wants to do. He’s not a kid.” The corner of Castiel’s mouth twitched into a small smile at Dean’s comment.

“It’s fine Charlie, I’ll go with Dean.” Castiel turned to Dean’s friends - they all looked angry with Dean - besides Benny who looked more annoyed. Castiel didn’t understand why a group of people his barely knew who choose his side over their own friend. Castiel was starting to guess that this was normal Dean behavior and they were sick of it.

Dean lead Castiel outside through the kitchen area, throwing a quick nod at a glaring Ellen and Jo.

Dean took a deep breath, staring at his feet. Castiel thought he looked like a scolded child, and he knew that look well.

Castiel leaned against the wall of the back alley waiting for Dean to speak.

“How are you getting home?” Dean looked up suddenly at Castiel.

“Uh, my driver… Frank is picking me up.” Castiel frowned at Dean’s question.

“Of course you have a driver,” Dean mumbled, clearly he couldn’t help himself but judge Castiel by his family. The teen should’ve been used to it by now. “What time are you done working?”

“Two hours,” Castiel answered quickly. "I'm on a little break now."

“Call…. _Frank_ …. tell him you have a ride. I’ll take you home.” Dean offered.

“Is that your way of an apology?” Castiel titled his head in confusion. Unsure of what Dean was trying to accomplish.

“Apology? I’m not apologizing Cas. I have nothing to apologize for, you should apologize for not telling me you’re working for my fucking family, or that my mother is now too unwell to continue working or… or that you’re fucking seventeen years old.”

“I’m sorry.” Dean looked surprised that Cas actually apologized, “I’m not sorry about working here or my age… but I’m really sorry about your mom. I don’t get along with mine but I couldn’t imagine …. losing her.”

“I’m sorry for yelling at you.” Dean answered back quickly.

Castiel smiled, “I can tell that was hard for you.” Dean rolled his eyes at the teen, “I accept. You can drive me home.”

“I-“ Dean shook his head, interrupting himself, “See ya later Cas,” he mumbled as he brushed past Castiel and back into the diner.

Their reunion wasn’t what Castiel wanted but Dean’s apology was a start.

* * *

After apologizing to Cas, Dean had received an earful of disappointments from Ellen, Jo, Charlie… Even Cole and Aaron had put in their two cents. Benny remained unsurprisingly quiet through everything. It was possible Benny wanted Cas gone as bad as Dean did.

“So you knew he was 17, right?” Cole asked out of concern.

“I didn’t know until the next morning, when he told me, I even drove the little shit to school,” Dean snorted out a humorous laugh, “High school.”

“Wait, wait,” Benny finally spoke, “The next morning?” The eyebrow raise forced a small _oh no_ from Dean. “He stayed the night?”

Charlie gasped with realization, “Oh my gosh, you’ve never let anyone stay the night before. That’s kinda cute,” She gushed.

“Chill Red, he had no where to go so I let him stay,” Dean shrugged, “What’s the big deal?”

“The big deal is that, you never ever care about where your conquest went after you were done with them.” Aaron said with an accusing tone.

“I couldn’t kick him out.. I mean, look at him!” Dean turned and pointed towards Cas who was taking an order form another table, “He’s all small and had these sad eyes…”

“Aww,” Cole placed a hand over his heart.

“I can’t believe I’m seeing the day the Grinch’s heart grew two sizes bigger,” Charlie stared dreamily at Dean.

“I hate you guys, so much,” Dean glanced at Benny, he looked angry, Benny had always been protective over Dean, especially after Alistair happened all those years ago.

When Dean drew his attention back to Aaron he was waving Castiel over.

“Hello,” Castiel said overly friendly, Dean almost felt proud that Cas didn’t seem as awkward as he did earlier. He seemed normal, and normal wasn’t a word Dean would ever use to describe Cas.

“So what was it like?” Cole asked, practically beaming at the kid.

“What was what like?” Castiel frowned and titled his head.

“Spending the night with the infamous Dean Winchester?” Charlie giggled and Dean rolled his eyes.

“Don’t answer them Cas,” He shook his head.

Cas smirked at Dean, and Dean learned quickly in that moment that he probably shouldn’t tell Cas what to do.

“What do you want to know about? The sex? The cuddling? The shower in the morning?” He grinned at his shocked friends.

“Oh my gosh!” Charlie bursted out laughing, “Cuddling!” She pushed on Dean’s arm in a teasing way.

“You fucked this kid in the shower after finding out he was 17?” Aaron snickered.

“No,” Dean snapped, “I found out after the shower and there was no-“ Dean threw his hands up, “Know what? I give up, have your guys' fun, I’ll just sit here.” He folded his arms over his chest, like a small pouting child.

“I’m sorry Dean,” Castiel smirked, the little shit wasn’t sorry.

That’s when Dean noticed, Castiel’s new name tag. It wasn’t printed on a small plaque of silver like Ellen and Jo’s, it was just a small piece of paper and hand written.

“Angel?” Dean questioned.

Cas looked down at his handmade nickname badge, “Oh yeah, I guess your mom called down to El- _Boss-lady_ with my new nickname. They liked it so-“ Castiel shrugged his shoulders.

“I like it,” Charlie nodded, “He does look like a little Angel.” Dean rolled his eyes.

“Yeah,” Cole agreed looking at Dean, “The kind you’d never kick out on the streets.” A hard kick under the table seemed to satisfy Dean’s annoyance.

* * *

Although Castiel enjoyed (most) of his first day he was happy his shit was finally over. Picking up his final checks from his tables he noticed how much more relaxed Dean seemed after his friends left, his legs were spread out in a booth all to himself picking at a second piece of pie. 

“You are going to pay for those, right?” Castiel said as he passed Dean’s table.

Dean chuckled, “Yeah, but my waiter was a but rude, probably won’t be getting a big tip.”

Castiel’s head titled at the filthy jokes he could tell, “File a formal complaint.” He turned sharply on his heal and headed towards the kitchen, he could hear Dean laughing behind him.

“You did great today!” Ellen pulled him into a hug as he talked into the kitchen, “Your really somthin’ you know that Angel?”

“I-thanks,” He blushed.

“So we’ll see you Monday after school?” Ellen asked in a demanding way.

“Of course,” Castiel nodded but still wasn’t completely sure how he was going to get away with spending so much of his free time at the diner.

“Great! See you then kid,” Ellen paused, “And don’t let Dean get to ya, his bark is bigger then his bite.”

“I know that.”

“Of course you do,” She patted his shoulder and helped him clock out.

* * *

Ten minutes into the, so far, silent car journey with Dean he started to look uncomfortable. Sure, Castiel was being unnaturally quiet but he didn’t expect his silence to make Dean unnerved.

“So uh-“ Dean side glanced at him, “I didn’t think about this but - Is your dad home?” Dean cleared his throat, an unnatural tell of awkwardness for Dean, “Should I drop you off around the corner? Do you secret service or something?”

“Or Something,” Castiel chuckled, “I have Frank. He works as both a sort of watcher and driver,” Cas sighed, “And my parents aren’t home, they won’t be all weekend.”

“That happen a lot?” Dean asked vaguely.

Castiel nodded before answering, “They’re in DC right now, they travel a lot, normally without me. I was raised by a series of nannies.”

“That… that sucks man, sounds… lonely.” Dean mumbled in a moment of sincerity.

Castiel stared at his profile for a moment in awe, “I’m very surprised you see it that way Dean.”

“Whatta mean?” Castiel smirked at Dean’s frown lines, he thought they were cute but definitely preferred his smile lines and the crinkle by his eyes. Castiel noticed that Dean didn’t genuinely smile too often.

“Poor little rich boy with his neglectful parents,” Castiel mocked and Dean winced.

“Money ain’t everything Cas.”

“No it is not,” Castiel took a quick glance out of his window, unintentionally hiding his face from Dean.

“You have siblings right?” Dean asked.

“Yes. I have three brothers and a sister.” Cas answered, “They’re all much older then me so I didn’t grow up with them.”

“Sucks, couldn’t imagine not being close to Sammy.”

“How’s the baby?” Cas asked in a subject change.

“Hael is doing great, she’s cute, Sammy sent me a video this morning,” Dean smiled, and this time it was a genuine one but Castiel couldn’t help but frown at how foreign and casual his sisters name sounded coming out of Dean’s mouth. Him and his family never mention Hael.

“You okay?” Dean tugged at Castiel’s sleeve, “You kinda zoned out.”

“Oh yeah, I’m fine. I’m happy to hear H-Hael is doing good.” Castiel stared out his window again, watching the passing buildings, “You’re lucky, you know, having a mother like yours.”

“I know,” Dean’s grip tightened on the wheel. An outward show of hiding emotions.

“What about your father?” Castiel asked in curiosity.

“He’s dead.” Dean answered fast and sharp.

“Oh, I’m very sorry Dean, I didn’t mean-“

“Drop it Cas, it’s fine, world’s better off.” Dean smirked and Castiel knew that one was fake.

“What was he like?” Castiel could guess. He learned from experience that most fathers are disappointments.

"He’s just - he’s not a good person.”

Castiel took in the fact Dean didn’t talk about his father in a past tense, he wondered why he was lying about his father being dead when he clearly wasn’t.

“I don’t want to talk about it,” Dean snapped before Castiel had the chance to say anything else.

“Okay, you don’t have to.” Castiel slouched in the front seat slightly, resting his head on the back.

“That was easy,” Dean gave him an odd look before bringing his eyes back to the road, it wasn’t too necessary for him to be looking because of the stopped traffic. Castiel figured he had no where else to look.

“What was easy?” Castiel mumbled, not realizing until that moment how tried he really was.

“You’re not gonna push me to open up about my daddy issues?” Dean chuckled, making another quick glance over at Castiel. They caught eyes briefly before Dean turned away.

“I won’t force you to talk to me Dean, I am not your therapist.” Castiel smiled at Dean’s loud outburst of laughter.

“Funny,” he said, his laugh fading to a smile, he looked at Castiel again, “Sometimes you act like a naive, innocent child and other times you act way beyond your years. You’re a weird kid Cas.”

“Sometimes you act like a tentative, sweet man, and other times you act like an asshole. You’re a weird guy Dean.” Castiel shot back, there was a moment of pause between to two before they both started laughing.

* * *

Their laughter barely died down before Cas fell asleep in the front seat, his head rested easily against the window, Dean stared at him for awhile wondering how someone could fall asleep that easy. Dean guessed the last few days had been unusually eventful for Cas.

The normal 20 minutes drive to Cas’ apartment was taking about an hour with the heavy early evening New York traffic. Cas slept the whole way, occasionally moving for moaning, the moaning wasn’t helping with ‘ _Operation don't fuck the high schooler again_ ’, but the teen making delicious noises it only reminded Dean what fun he could be having with Cas instead of driving him home like his fucking chaperone.

“Cas?” Dean shook his shoulder. Cas jumped up comically with wide eyes staring at Dean.

“We’re here sleeping beauty,” Dean chuckled.

Cas rubbed his eyes with the heal of his hands, frowning adorably. “I don’t even remember falling asleep,” he mumbled.

“Yeah buddy, you were out, didn’t even wake to the sweet sounds of Led Zeppelin.” Dean patted his shoulder.

Cas smirked before frowning, “I was hoping we would be able to talk more.”

That was the opposite of what Dean wanted, the topics Cas wanted to talk about was not something Dean was willing to share - like his father.   
“You’ll be seeing me again,” Dean shrugged a shoulder, “And you’ve got my number so-“

“You never gave me your number,” Cas quickly corrected him.

“Oh yeah, give me your phone,” This was inevitable, Dean knew that. Cas smiled and quickly dug his phone out go his pocket and handed it over to Dean.

Dean punched in his number and saved it before handing it back to Cas.

“Thanks,” The teen mumbled with a stupid smile on his face.

“Don’t make me regret that Cas,” Dean warned playfully, he knew he was going to regret it.

“I won’t annoy you,” Cas paused, “Actually I can’t promise you that.” He winced as Dean laughed.

“I didn’t expect-“ Dean froze win sentence when he felt a warm hand on his thigh, he turned his head to find that Cas slid over closer to him.

“Uh-“ He stammered dumbly, not stopping Cas as he leaned in placing a chaste kiss on Dean’s mouth and in a moment of weakness for Dean - _he kissed back_. As soon as Cas pulled away from the chaste kiss, he was already leaning back in but with more intent in his eyes.

Just as Cas’ lips touched his again Dean came to his senses and pushed Cas away gently. The frown on the teens face made Dean look away quickly.

“That can’t happen Cas,” Dean shook his head as if he were scolding a child - jesus, he _was_ scolding a child.

“Yeah, I know,” Cas responded with a disappointed sigh.

“Then why’d you do it?” Dean called almost playfully. Could he just not stay mad at this guy?

“Opportunist,” Cas smirked, “and I wanted to see if you’d kiss back, I hoped you would and I’m glad you did.”

Dean rolled his eyes, “Get out,” He said without malice.

“Bye Dean,” Cas said deeply, he leaned back over towards Dean, surprising the older man with a quick peck on the cheek before exiting the car.

He watched Cas carefully as he talked to the doorman of his building, Cas was all animated and seemingly untouched by the harsh world. Dean remembered a time he was like that too, a time before his father’s drinking problem, a time before Alistair fucked him up. He imagined himself ruining Cas the way Alistair did to him, he shivered involuntarily, he would never want Cas to go through something like that. Dean was knee deep in muddy water when it came to the teen, but one thing he knew for sure, he could and would never be Alistair, and he certainly couldn’t be what Cas wanted him to be.

A text message went off on Dean’s phone, he was so deep in thought he hadn’t noticed Cas had already disappeared into his building.

**Unknown: Hi Dean :)**

Dean smiled at his phone before he could stop himself.

**Unknown: This is Castiel by the way. I forgot to give you my number. Now you have it.**

Dean sent back a quick, _I know Cas_ , and, _Goodnight Cas_ , before saving the teens number in his phone under the contact name ‘ _Angel_ ’.


End file.
